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ChemicalBook CAS DataBase List acromelic acid A
86630-09-3

acromelic acid A synthesis

2synthesis methods
4-Pentyn-2-ol, 5-(6-methyl-3-pyridinyl)-1-(phenylmethoxy)-, (R)- (9CI)

109552-75-2
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acromelic acid A

86630-09-3
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Yield:-

Steps:

Multi-step reaction with 15 steps
1: 85 percent / H2, quinoline / Lindlar catalyst / benzene / 24 h / Ambient temperature
2: Et3N / CH2Cl2 / 2 h / 0 °C
3: CH2Cl2 / 2 h / 0 °C
4: 73 percent / 1,2-dichloro-benzene / 1.5 h / 200 °C
5: H2, HCl / 10percent Pd-C / methanol / 72 h / Ambient temperature
6: 3 N NaOH / dioxane / 1 h / Ambient temperature
7: 1.) aqueous NaIO4, 2.) aq. KMnO4 / 1.) 0 deg C, 15 min, 2.) 0 deg C, 2 h
8: c.c H2SO4 / 24 h / Heating
9: Et3N / CH2Cl2 / 0.25 h / Ambient temperature
10: 94 percent / NaH, DBu / benzene / 5 h / Ambient temperature
11: m-CPBA / CH2Cl2 / 24 h / Ambient temperature
13: m-CPBA / CH2Cl2
14: trifluoroacetic anhydride / dimethylformamide / 45 h / Ambient temperature

References:

Takano, Seiichi;Iwabuchi, Yoshiharu;Ogasawara, Kunio [Journal of the American Chemical Society,1987,vol. 109,# 18,p. 5523 - 5524]

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