Water → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 409484노트

반응식

HRID 409484 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.[OH2:21]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:13][O:21][C:9]([CH:6]1[CH2:7][CH2:8][CH:3]([CH2:11][OH:12])[CH2:4][CH2:5]1)=[O:10].[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

8

반응물 4

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

생성물 2

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl esterHCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

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 h while warming to room temperature. Benzyl bromide (1.2 mL, 10 mmol) is added dropwise followed by tetrabutylammonium iodide (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 aqueous layer is extracted with EtOAc. The combined organic layer (dried with MgSO4) is concentrated. The desired product, (4-benzyloxymethyl-cyclohexyl)-methanol, is obtained (1.40 g, 60%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

후처리

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

출처 및 근거

ORD 기록
ord-e5992f3a6b994186a626a749be4310e0
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759365B2

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