Benzo(B)Thiophene → a-(2-Benzo[b]thienyl)-3,4-dimethoxybenzyl alcohol

HRID 1166906Notes

Reaction equation

HRID 1166906 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:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:20]=[O:21]>C1COCC1>[S:1]1[C:5]([CH:20]([OH:21])[C:19]2[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:17]([O:16][CH3:15])[CH:18]=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 8419VeratraldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 49962621a-(2-Benzo[b]thienyl)-3,4-dimethoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

a-(2-benzo[b]thienyl)-3,4-dimethoxybenzyl alcohol was prepared in the same manner as described in Example 40A. Reaction of benzo[b]-thiophene (7.5 mmoles, 1.0 g), t-BuLi (1.7 m, 97 mmoles, 5.7 ml) and 3,4-dimethoxybenzaldehyde (8.9 mmoles, 1.5 g) in THF (20 ml) yielded, after flash chromatography using 30% ethyl acetate/hexanes, 2.25 g (≈100%) of a white gummy solid.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-e633627e1f464379a39f73275ec5e19e
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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