Water → ((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

HRID 217236노트

반응식

HRID 217236 반응식
[H-].[Na+].[C@H:3]1([CH2:11][OH:12])[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:13]([O:10][CH2:9][CH:6]1[CH2:7][CH2:8][CH:3]([CH2:11][OH:12])[CH2:4][CH2:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178520956HCID 178520956, 화합물

생성물 1

HCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol수율 60%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a slurry of NaH (440 mg, 11 mmol) in THF (22 mL) is added trans-1,4-cyclohexanedimethanol (1.44 g, 10 mmol) at 0° C., and the mixture is stirred for 1 hour while warming to room temperature. Benzyl bromide (1.2 mL, 10 mmol) is added dropwise followed by TBAI (185 mg, 0.5 mmol). The reaction is heated to 60° C. for 15 hours. After cooling to room temperature, H2O is added, and the mixture is extracted with EtOAc. The combined organic layer after dried over MgSO4 is concentrated to obtain (4-benzyloxymethyl-cyclohexyl)-methanol as clear oil (1.40 g, 60%) after purification.

후처리

  1. temperatureThe reaction is heated to 60° C. for 15 hours
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture is extracted with EtOAc
  4. dry with materialThe combined organic layer after dried over MgSO4
  5. concentrationis concentrated

출처 및 근거

ORD 기록
ord-ba6535fc556644678cb7ac7c0f4a84b8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193349B2

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