Hydrogen Peroxide → 2-(4-Benzyloxy-phenyl)-3-ethyl-5-hydroxymethyl-4-methyl-cyclohexanol

HRID 351441

反応式

HRID 351441 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]([CH2:21][CH3:22])[CH:19]([CH3:23])[CH:18]([CH2:24][OH:25])[CH2:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C)C.[OH-:29].[Na+].OO>C1COCC1.C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH:20]([CH2:21][CH3:22])[CH:19]([CH3:23])[CH:18]([CH2:24][OH:25])[CH2:17][CH:16]2[OH:29])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 18436344[4-(4-Benzyloxy-phenyl)-5-ethyl-6-methyl-cyclohex-3-enyl]-methanol

生成物 1

HCID 184363332-(4-Benzyloxy-phenyl)-3-ethyl-5-hydroxymethyl-4-methyl-cyclohexanol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
0 °C

実験手順

To the solution of [4-(4-benzyloxy-phenyl)-5-ethyl-6-methyl-cyclohex-3-enyl]-methanol (3.1 g, 6.8 mmol) in THF (50 mL) was added BH3.S(CH3)2 solution (1.0 M in THF, 10.3 mL, 1.5 eq.) at 0° C. The reaction mixture was refluxed for 4 h and then cooled to 0° C. NaOH (20% aqueous, 30 mL) and H2O2 (50% in H2O, 21 mL) were added at 0° C. The reaction mixture was then stirred at 0˜25° C. for 4 h. The reaction mixture was then diluted with ethyl acetate/H2O (400 mL/200 mL). The organic layer was separated, dried over MgSO4 and purified on SiO2 (50˜100% ethyl acetate/hexane) to yield 2-(4-benzyloxy-phenyl)-3-ethyl-5-hydroxymethyl-4-methyl-cyclohexanol.

後処理

  1. customat 0° C
  2. temperatureThe reaction mixture was refluxed for 4 h
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. custompurified on SiO2 (50˜100% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-73f1c5ea53c54f169e78a3de55763651
出典データセット
uspto-grants-2007_02
特許番号
US07183445B2

関連ノート

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