Benzo(B)Thiophene → HCID 53641103, compound

HRID 234392Notes

Reaction equation

HRID 234392 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.CO[C:17]1[CH:18]=[C:19]([CH:22]=CC=1OC)[CH:20]=O.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[S:1]1[C:5]([CH:29]([OH:30])[C:28]2[CH:27]=[CH:31][C:18]([CH3:17])=[C:19]([CH3:22])[CH:20]=2)=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 4

HCID 7221Benzo(B)ThiopheneHCID 8028TetrahydrofuranHCID 8419VeratraldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 53641103HCID 53641103, compound

Procedure

α-(2-benzo[b]thienyl)-3,4-dimethylbenzyl 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 aceteate/hexanes, 2.25 g (≈100%) of a white gummy solid.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-5697b1093c504b89bdb1827d0503c2fc
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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