2-Thiophenecarboxaldehyde → 11-(2-Thienyl)-10-undecenoic acid

HRID 377497

반응식

HRID 377497 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[Br-].[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:11])=[O:10]>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]([OH:11])=[O:10]

참가 물질

4

반응물 2

HCID 73642-ThiophenecarboxaldehydeHCID 18795071(9-Carboxynonyl)(triphenyl)phosphanium bromide

생성물 1

HCID 5421593011-(2-Thienyl)-10-undecenoic acid수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

This compound was synthesized from 2-thiophenecarboxaldehyde (2.24 g, 20 mmol) and 9-carboxynonyltriphenylphosphonium bromide (10.27 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (hexanes-ethyl acetate) afforded the product (2.45 g, 46%) as white crystals (mp 61-62° C.); IR: 3450-2500, 1715 cm-1 ; 1H-NMR: 1.31 (m, 8H), 1.45 (m, 2H), 1.65 (m, 2H), 2.34 (t, 2H), 2.38 (t, 2H), 5.55 (m, 1H), 6.50 (d, 1H), 6.95 (m, 2H), 7.23 (d, 2H), 10.05 (bs, 1H). Anal. Calcd. for C15H22O2S: C, 67.63, H, 8.32%; Found: C, 67.60, H, 8.34%. Z:E=19:81.

후처리

  1. customCrystallization (hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-2b60d0cc8a3e4590954822a22b68d817
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025511

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