2-Thiophenecarboxaldehyde → 9-(2-Thienyl)-8-nonenoic acid

HRID 1004477Notes

Reaction equation

HRID 1004477 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]=O>C1COCC1>[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 11317723(7-Carboxyheptyl)triphenylphosphonium bromide

Product 1

HCID 538570579-(2-Thienyl)-8-nonenoic acidYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from 7-carboxyheptyltriphenylphosphonium bromide (9.71 g, 20 mmol) and 2-thiophenecarboxaldehyde (2.24 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization afforded the product (2.79 g, 59%) as white crystals (mp 45-46° C.). IR: 3400-2500, 1720, 710 cm-1 ; 1H-NMR: 1.45 (m, 8H), 2.35 (m, 4H), 5.55 (m, 1H), 6.50 (d, 1H), 7.00 (m, 3H), 11.00 (bs, 1H). Anal. Calcd. for C13H18SO2 : C, 65.51, H, 7.61%; Found: C, 65.58, H, 7.63%. Z:E=75:25.

Workup

  1. customCrystallization

Sources & evidence

ORD record
ord-a4c8ec40a16a40b6b668505cd2b8f78c
Source dataset
uspto-grants-2000_04
Patent number
US06048989

Reaction notes

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