Methanol → 4-(Hydroxymethyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1186428ノート

反応式

HRID 1186428 の反応式
[C:1]([C:3]1([C:9](OC)=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].CO.O.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]

参加物

7

反応物 4

HCID 887MethanolHCID 962Water2 回HCID 4311764Sodium borohydrideHCID 16726727Methyl 4-cyanooxane-4-carboxylate

生成物 1

HCID 249369984-(Hydroxymethyl)tetrahydro-2H-pyran-4-carbonitrile収率 92%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (2.93 g, 17.3 mmol) was dissolved in tetrahydrofuran (50 mL), methanol (10 mL) and water (5.0 mL). To this, sodium borohydride (1.31 g, 34.6 mmol) was added and the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by addition of water to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give 4-cyanotetrahydro-2H-pyran-4-ylmethanol (1.59 g, yield: 92%).

後処理

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-e0a4dcaf845e4ea990aabfca7bdeca90
出典データセット
uspto-grants-2014_03
特許番号
US08673908B2

反応ノート

読み込み中…