Water → (4-(Benzyloxy)-3-fluorophenyl)methanol

HRID 901164ノート

反応式

HRID 901164 の反応式
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[F:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C.O>C(O)C.C1COCC1>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][C:12]=1[F:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 219768984-(Benzyloxy)-3-fluorobenzaldehyde

生成物 1

HCID 21976875(4-(Benzyloxy)-3-fluorophenyl)methanol

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium borohydride (500 mg, 13.2 mmol) was added to a solution of 4-benzyloxy-3-fluoro-benzaldehyde (CAB03016, 7.32 g, 31.8 mmol) in ethanol (40 mL) and THF (40 mL) at 0° C. The clear and colourless solution was allowed to warm to room temperature and stirred for 12 h at this temperature. Ethyl acetate (150 mL) and water (50 mL) were added to the solution, the organic layer was separated, washed with water (2×50 mL) and brine (50 mL), dried over sodium sulphate and concentrated under reduced pressure. The white solid residue was dissolved in dichloromethane and precipitated by addition of hexane. The white powder was filtered off and dried under high vacuum. Yield: 7.16 g (97%). 1H-NMR (400 MHz, CDCl3) δ=1.71 (s, 1H, —OH), 4.61 (s, 2H, —CH2OH), 5.15 (s, 2H), 6.97 (dd, J=8.6, 8.6 Hz, 1H), 7.02 (dd, J=8.6, 1.9 Hz, 1H), 7.13 (dd, J=11.7, 1.9 Hz, 1H), 7.30-7.46 (m, 5H). LRMS (FAB+): 91 (100), 215.1 (40), 232.1 (100, [M]+).

後処理

  1. customthe organic layer was separated
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe white solid residue was dissolved in dichloromethane
  6. customprecipitated by addition of hexane
  7. filtrationThe white powder was filtered off
  8. customdried under high vacuum

出典と根拠

ORDレコード
ord-4843ceb8c5be403ebc3149f79c348677
出典データセット
uspto-grants-2008_04
特許番号
US07361677B2

反応ノート

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