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4-Pentylcyclohexanal → 2-Benzyloxy-6-[2-(4-pentyl-cyclohexyl)-vinyl]-naphthalene

HRID 48105
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인쇄 미리보기

반응식

HRID 48105 반응식
[Br-].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH:14]=[CH:13]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:40]([CH:45]1[CH2:50][CH2:49][CH:48]([CH:51]=O)[CH2:47][CH2:46]1)[CH2:41][CH2:42][CH2:43][CH3:44].CC(C)([O-])C.[K+]>COC(C)(C)C>[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:20]=[CH:51][CH:48]3[CH2:47][CH2:46][CH:45]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:50][CH2:49]3)[CH:16]=2)[CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
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참가 물질

5

반응물 3

HCID 140856594-PentylcyclohexanalHCID 20632177(6-Benzyloxynaphthalen-2-ylmethyl)-triphenyl-phosphonium BromideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 698847882-Benzyloxy-6-[2-(4-pentyl-cyclohexyl)-vinyl]-naphthalene수율 74%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

The solution of (6-benzyloxy-naphthalen-2-ylmethyl)-triphenyl-phosphonium bromide (19) (1 equi.), 4-pentyl-cyclohexanecarboxaldehyde (22), and potassium tert-butoxide (1.3 equi.) in tert-butyl methyl ether (6 mL/mmole) was stirred at room temperature for 24 h, then quenched with water, extracted with diethyl ether, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (1.25% EtOAc/hexane) afforded 2-benzyloxy-6-[2-(4-pentyl-cyclohexyl)-vinyl]-naphthalene (23) as a white solid (74%).

후처리

  1. customquenched with water
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (1.25% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-f6c63d21095849468799f3cf0417b9fa
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06703082B1

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