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

HRID 409484ノート

反応式

HRID 409484 の反応式
[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

参加物

8

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178520956HCID 178520956、化合物

生成物 2

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e5992f3a6b994186a626a749be4310e0
出典データセット
uspto-grants-2014_06
特許番号
US08759365B2

反応ノート

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