Ammonium Chloride → Tert-butyl 3-chloro-4-(3-hydroxycyclohexyl)benzoate

HRID 1849763ノート

反応式

HRID 1849763 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Na].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 86703645Tert-butyl 3-chloro-4-(3-oxocyclohexyl)benzoate

生成物 1

HCID 86703646Tert-butyl 3-chloro-4-(3-hydroxycyclohexyl)benzoate収率 53%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a mixture of tert-butyl 3-chloro-4-(3-oxocyclohexyl)benzoate in anhydrous methanol (50 mL) was added sodium borobydride (1.04 g, 27.40 mmol) at 0° C. The reaction mixture was stirred for 1 hour at 0° C., after which saturated ammonium chloride solution (10 mL) was added. All volatiles were evaporated under reduced pressure, and the residue was partitioned between ethyl acetate (200 mL) and water (20 mL). The organic phase was washed with brine (10 mL), dried over sodium sulfate, and filtered. Concentration under reduced pressure gave a residue which was purified by silica gel column chromatography using 0-40% ethyl acetate in hexanes as eluent to afford the title compound as colorless oil (2.24 g, 53%): 1H NMR (300 MHz, CDCl3) δ 7.94-7.92 (m, 1H), 7.84-7.79 (m, 1H), 7.32-7.27 (m, 1H), 3.85-3.69 (m, 1H), 3.16-3.03 (m, 1H), 2.19-2.04 (m, 2H), 1.96-1.77 (m, 2H), 1.63-1.18 (m, 14H); MS (ES+) m/z 255.2, 257.1 (M−55).

後処理

  1. customAll volatiles were evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (200 mL) and water (20 mL)
  3. washThe organic phase was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationConcentration under reduced pressure
  7. customgave a residue which
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d314e415009d49d2ba5b6c004fdc9f4a
出典データセット
uspto-grants-2015_02
特許番号
US08952169B2

反応ノート

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