Ethyl Bromide → 7-Hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne

HRID 26177

반응식

HRID 26177 반응식
C(Br)C.[Mg].[OH:5][C:6]([CH3:16])([CH:9]=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=[CH2:14])[C:7]#[CH:8].[CH3:17][C:18]1([CH3:26])[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[C:19]1=[O:25].[Cl-].[NH4+]>C(OCC)C.C1C=CC=CC=1>[OH:5][C:6]([CH3:16])([C:7]#[C:8][C:19]1([OH:25])[CH:20]([CH3:24])[CH2:21][CH2:22][CH2:23][C:18]1([CH3:26])[CH3:17])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=[CH2:14]

참가 물질

8

반응물 5

HCID 6332Ethyl BromideHCID 170002,2,6-TrimethylcyclohexanoneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 542483613,7-Dimethylnona-4,6,8-trien-1-yn-3-ol

생성물 1

HCID 543180627-Hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 3283Diethyl Ether용매2회

실험 절차

A solution of ethyl bromide (1.75 g.) in diethyl ether was added to a suspension of magnesium (0.385 g.) in ether and the mixture was heated to reflux for 30 minutes. A solution of the alcohol, 3-hydroxy-3,7-dimethyl-nona-4,6,8-trien-1-yne, (1.0 g.) in dry benzene was added and the mixture refluxed 30 minutes. A solution of 2,2,6-trimethylcyclohexanone (1.12 g.) in benzene was added and the mixture refluxed for 15 minutes and poured into saturated aqueous ammonium chloride solution. The organic phase was washed with brine dried and concentrated to give 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne which was chromatographed on activity III alumina to give pure 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethyl-cyclohexyl)-nona-1,3,5-trien-8-yne.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture refluxed 30 minutes
  4. temperaturethe mixture refluxed for 15 minutes
  5. washThe organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-35cc3eed3fdd4c9c830572cf9db82737
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04148829

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