ChemicalBook CAS DataBase List tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate synthesis

11synthesis methods

Product Name:tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate
CAS Number:124752-23-4
Molecular formula:C13H22O5
Molecular Weight:258.31

154026-95-6 Synthesis

tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

154026-95-6
252 suppliers
$9.00/5g

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate

124752-23-4
230 suppliers
$9.00/250mg

Yield:124752-23-4 96.1%

Reaction Conditions:

Stage #1:(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester with methanol;potassium carbonate for 3 h;
Stage #2: with sodium hypochlorite;2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;sodium hydrogencarbonate;potassium bromide in dichloromethane at -5 - 5; for 1 h;

Steps:

11 Example 11
In a 500 mL three-necked flask, 10 g of D-5, 100 mL of methanol and 4.0 g of potassium carbonate were successively added, and the mixture was stirred for 3 hours, filtered, and the filtrate was concentrated to dryness under reduced pressure at 35 to 45 °C.The resulting syrup was dissolved in 150 mL of dichloromethane, and 3.0 g of sodium hydrogencarbonate, 0.5 g of potassium bromide and 0.4 g of TEMPO were sequentially added.After the mixture was stirred and cooled to -5 to 5 ° C, 50.0 g of an 8% sodium hypochlorite solution was added dropwise.After the completion of the dropwise addition, the mixture was stirred at -5 to 5 ° C for 1 hour.The reaction was monitored by TLC, and the reaction was quenched by the addition of 0.7 g of sodium thiosulfate and 10.0 g of water.The layers were static and the aqueous layer was stripped with 100 mL of dichloromethane.The organic layers were combined and the organic layer was washed with 2×200 mL water.The washed organic layer was dried under reduced pressure at 35 to 45 ° C to give a pale red solid 8.2 g of D-7, yield 96.1%.

References:

Zhejiang Hongyuan Pharmaceutical Co., Ltd.;Mei Guangyao;Wang Haibo;Jin Hui;Kuang Hongfu;Wang Yabin;Miao Hanhui;Xu Chenli CN109574830, 2019, A Location in patent:Paragraph 0083-0085

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124655-09-0 Synthesis