Sodium borohydride → Methyl 4-[3-(hydroxymethyl)phenyl]benzoate

HRID 1860015ノート

反応式

HRID 1860015 の反応式
[BH4-].[Na+].[CH:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]>C(O)C>[OH:4][CH2:3][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 4321386Methyl 4-(3-formylphenyl)benzoate

生成物 1

HCID 1392389Methyl 4-[3-(hydroxymethyl)phenyl]benzoate収率 71.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Sodium borohydride (132 mg) was added to a solution of methyl 3′-formylbiphenyl-4-carboxylate (720 mg), which is the product of Reference example 14(a), in ethanol (50 ml) at ambient temperature. The mixture was stirred under an atmosphere of nitrogen for 50 minutes. The reaction mixture was quenched with 50% acetic acid and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to afford the desired compound (522 mg) as colorless crystals.

後処理

  1. customat ambient temperature
  2. customThe reaction mixture was quenched with 50% acetic acid
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe layers were separated
  6. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-613ebbfcf39a474f9a3effd1a7a8d645
出典データセット
uspto-grants-2003_03
特許番号
US06528525B1

反応ノート

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