Benzo(B)Thiophene → a-(2-Benzo[b]thienyl)-4-methoxybenzyl alcohol

HRID 234394Notes

Reaction equation

HRID 234394 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[Li]C(C)(C)C.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1>C1COCC1>[S:1]1[C:5]([CH:21]([OH:22])[C:20]2[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 312444-MethoxybenzaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 49962600a-(2-Benzo[b]thienyl)-4-methoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-(2-benzo[b]thienyl)-4-methyoxybenzyl alcohol was prepared by the method of Example 40A with benzo[b]thiophene (7.5 mmoles. 1.0 g), t-BuLi (1.7 m, 10.4 mmoles, 6.1 ml), 4-methoxy-benzaldehyde (8.9 mmoles, 1.1 ml) and THF (20 ml). Flash chromatography (20% ethyl acetate/hexanes) provided 1.75 g (87%) of a yellow solid.

Sources & evidence

ORD record
ord-37332010471e49eebb1b071be2d0b932
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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