3,4,5-Trimethoxybenzaldehyde → HCID 49962541, compound

HRID 234385Notes

Reaction equation

HRID 234385 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]=[C:23]([O:27][CH3:28])[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:18]=[C:17]([O:16][CH3:15])[C:24]([O:25][CH3:26])=[C:23]([O:27][CH3:28])[CH:22]=2)=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 7221Benzo(B)ThiopheneHCID 178418306HCID 178418306, compound

Product 1

HCID 49962541HCID 49962541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-(2-benzo[b]thienyl)-3,4,5-trimethoxybenzyl 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 (1.7m, 9.7 mmoles, 5.7 mls) and 3,4,5-trimethoxybenzaldehyde (8.9 mmoles, 1.8 g) in THF (20 ml) yielded, after flash chromatography using 50% ethyl acetate/hexanes, 2.4 g (97%) of a yellow-white solid.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-bf3d8a8104194d6ab788bf02565ee542
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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