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Water → 17-Bromoheptadec-6-en-1-ol

HRID 1756487
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HRID 1756487 반응식
[Br-].[OH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[Br:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]O.O>ClCCl.O1CCCC1>[Br:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 7416311-Bromo-1-undecanolHCID 2784664Phosphonium, (6-hydroxyhexyl)triphenyl-, bromideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 5368882717-Bromoheptadec-6-en-1-ol수율 45.8%

시약·촉매·용매 2

HCID 6344Dichloromethane
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of (6-hydroxyhexyl)triphenylphosphonium bromide (5.0 g) in dichloromethane (20 ml) was added dropwise to a mixture of potassium tertiary-butoxide (2.8 g) in tetrahydrofuran (100 ml) at 5°. After ten minutes, 11-bromoundecanol (2.8 g) in tetrahydrofuran (20 ml) was added and the reaction stirred at 5° until TLC indicated completion of the reaction. Water (20 ml) was added and the mixture then concentrated in vacuo. Water (20 ml) was added to the residue and the aqueous phase extracted with ether (2×50 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a brown oil. This was subjected to column chromatography to yield 17-bromoheptadec-6-en-1-ol (1.7 g, 45%).

후처리

  1. waitAfter ten minutes
  2. customcompletion of the reaction
  3. concentrationthe mixture then concentrated in vacuo
  4. additionWater (20 ml) was added to the residue
  5. extractionthe aqueous phase extracted with ether (2×50 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil

출처 및 근거

ORD 기록
ord-3d8c8c6c97a24d6d99f70e7075a22ca2
출처 데이터셋
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05441731

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