Lithium aluminum hydride → 2-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanol

HRID 713982ノート

反応式

HRID 713982 の反応式
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH:17]3[CH2:22][CH2:21][CH:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:19][CH2:18]3)[CH:12]=2)[CH:7]=1)C.[AlH4-].[Li+]>C1COCC1>[C:23]([CH:20]1[CH2:21][CH2:22][CH:17]([O:16][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[CH:7]=[C:6]([CH2:5][CH2:4][OH:3])[CH:15]=[CH:14]3)[CH2:18][CH2:19]1)([CH3:26])([CH3:24])[CH3:25]

参加物

4

反応物 2

HCID 28112Lithium aluminum hydrideHCID 66926519[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetic acid ethyl ester

生成物 1

HCID 669266452-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanol収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of [6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-acetic acid ethyl ester (250 mg, 0.68 mmol) in THF (10 mL) was added 1.0 M of lithium tetrahydroaluminate in THF (2 mL, 2 mmol) at 0° C. After stirred at room temperature for 2 hrs, the solution was quenched with ethyl acetate (1 mL), then added Rochelle's salt aqueous (1.5 mL). The solution was stirred for 1 hr, then extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated. The resulting crude was purified via silica gel column eluted with EtOAc in hexanes from 0 to 60% to give white precipitate (0.17 g, yield: 77%). ESI-MS: 327.20 (M+H)+.

後処理

  1. customthe solution was quenched with ethyl acetate (1 mL)
  2. stirringThe solution was stirred for 1 hr
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude was purified via silica gel column
  8. washeluted with EtOAc in hexanes from 0 to 60%

出典と根拠

ORDレコード
ord-2aeaeb20c55d447493a6007b2b23ad51
出典データセット
uspto-grants-2015_11
特許番号
US09186367B2

反応ノート

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