Tetrahydrofuran → 4-Hydroxy-4'-(1-hydroxyethyl)biphenyl

HRID 2380166ノート

反応式

HRID 2380166 の反応式
C(O[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.[O:18]1CC[CH2:20][CH2:19]1.[BH4-].[Na+]>CO>[OH:18][CH:19]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)[CH3:20]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 144384094-Methylcarbonyloxy-4'-hydroxybiphenyl

生成物 1

HCID 139308004-Hydroxy-4'-(1-hydroxyethyl)biphenyl収率 92.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution containing 4-acetoxy-4'-hydroxy-1,1'-biphenyl from part A (5.0 g, 23.6 mmol) in methanol (500 mL) and tetrahydrofuran (30 mL) is treated with sodium borohydride (0.9 g, 23.8 mmol) in portions over 30 minutes at room temperature. After 2 hours, the reaction mixture is concentrated under reduced pressure, diluted with water (400 mL), acidified with 2N HCl and extracted with ethyl acetate. The organic layer is washed with water and brine, dried over MgSO4 and concentrated to a solid residue. Crystallization of the solid from ethyl acetate gives 4.7 g (92.9%) of the title compound, m.p. 159°-160° C.; MS (El m/z): 214 (M)+ and 199 (b.p. M-CH3)+.

後処理

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additiondiluted with water (400 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a solid residue
  7. customCrystallization of the solid from ethyl acetate

出典と根拠

ORDレコード
ord-c862cfaf2d8e4603b188723b52d51107
出典データセット
uspto-grants-1994_11
特許番号
US05364944

反応ノート

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