4,5,6,7-tetrahydro-1-benzothiophene-3-carbaldehyde(SALTDATA: FREE) synthesis

3synthesis methods

Product Name:4,5,6,7-tetrahydro-1-benzothiophene-3-carbaldehyde(SALTDATA: FREE)
CAS Number:851634-60-1
Molecular formula:C9H10OS
Molecular Weight:166.24

(4,5,6,7-tetrahydro-1-benzothiophen-3-yl)methanol

851634-59-8
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4,5,6,7-tetrahydro-1-benzothiophene-3-carbaldehyde(SALTDATA: FREE)

851634-60-1
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$45.00/50mg

Yield:851634-60-1 88%

Reaction Conditions:

Stage #1: (4,5,6,7-tetrahydrobenzo[b]thiophene-3-yl)methanolwith Dess-Martin periodane in dichloromethane at 20; for 0.333333 h;
Stage #2: with sodium hydroxide in diethyl ether;dichloromethane;water; for 0.25 h;

Steps:

28.2

;A solution of 4,5,6,7-tetrahydro-1-benzothien-3-ylmethanol (Step 1, 320 mg, 1.9 mmol) in dichloromethane (10 mL) was added to a stirred solution of 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.92 g, 2.1 mmol) in dichloromethane (10 mL) under nitrogen and stirred at room temperature for 20 minutes. Diethyl ether (50 mL) and 1N sodium hydroxide solution (25 mL) were added and the mixture stirred vigorously for 15 minutes. The organic layer was washed with sodium hydroxide, water and brine, dried over MgSO₄ and evaporated in vacuo to give 4,5,6,7-tetrahydro-1-benzothiophene-3-carbaldehyde (280 mg, 88%). ¹H NMR (360 MHz, CDCl₃) δ 9.88 (1H, s), 7.85 (1H, s), 2.92-2.88 (2H, m), 2.76 (2H, t, J=6.0 Hz), 1.88-1.76 (4H, m).

References:

US2005/101586,2005,A1 Location in patent:Page/Page column 13

Ethyl 4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

14559-12-7
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851634-60-1
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References

4506-71-2 Synthesis

ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE

4506-71-2
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851634-60-1
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References