3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol → 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcycloheptanone

HRID 1074492노트

반응식

HRID 1074492 반응식
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18]CCC)[CH:12]=[CH:11][C:10]=1[CH:24]1[CH:29]([CH3:30])[CH:28]([CH3:31])[CH2:27][C:26]([CH:33](Br)Br)([OH:32])[CH2:25]1)C1C=CC=CC=1.[CH2:36]([Li])[CH2:37][CH2:38][CH3:39]>O1CCCC1>[CH2:36]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:11][CH2:12][CH3:13])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH:29]([CH3:30])[CH:28]([CH3:31])[CH2:27][CH2:33][C:26](=[O:32])[CH2:25]1)[C:37]1[CH:14]=[CH:9][CH:10]=[CH:39][CH:38]=1

참가 물질

4

반응물 2

HCID 204969043-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanolHCID 178418339Butyllithium

생성물 1

HCID 204968973-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcycloheptanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a -78° C. solution of 30.4 g (0.050 mole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol in 150 ml of tetrahydrofuran is slowly added over a period of 2 hours 47.7 ml (0.105 mole) of n-butyllithium (2.2 M in hexane). The reaction solution is stirred 2 hours longer at -78° C. and 10 minutes at 0° C. and then quenched by pouring into 300 ml of ice cold 1 N hydrochloric acid. The quenched reaction is extracted with two 250 ml portions of ether, the combined extract washed with 250 ml of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 500 g of silica gel eluted with ether-pentane to yield the title compound.

후처리

  1. customquenched
  2. additionby pouring into 300 ml of ice cold 1 N hydrochloric acid
  3. customThe quenched reaction
  4. extractionis extracted with two 250 ml portions of ether
  5. extractionthe combined extract
  6. washwashed with 250 ml of saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue is purified via column chromatography on 500 g of silica gel
  10. washeluted with ether-pentane

출처 및 근거

ORD 기록
ord-2a9dd04b9afd47c38accb619fb491a0b
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04391827

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