Methanol → HCID 86647826、化合物

HRID 241071ノート

反応式

HRID 241071 の反応式
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH:12]=C)[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1.[BH4-].[Na+].C[OH:17]>ClCCl>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH2:12][OH:17])[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866478274-Chloro-7-vinyl-5,6,7,8-tetrahydroquinazoline

生成物 1

HCID 86647826HCID 86647826、化合物収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ozone was bubbled through a cooled (−78° C.) solution of 4-chloro-7-vinyl-5,6,7,8-tetrahydroquinazoline (reagent preparation 3, 0.35 g, 1.8 mmol) in methanol (5 mL) and dichloromethane (30 mL) until a blue color persisted. The solution was then sparged with N2 for 10 minutes and sodium borohydride (0.14 g, 3.6 mmol) was added portionwise. After 30 minutes the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and then concentrated in vacuo to provide (4-chloro-5,6,7,8-tetrahydroquinazolin-7-yl)methanol (0.32 g, 90% yield) as a waxy solid. MS (ES) for C9H11ClN2O: 199 (MH+).

後処理

  1. customOzone was bubbled through
  2. customThe solution was then sparged with N2 for 10 minutes
  3. customAfter 30 minutes the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1ae047abe0194348bcddfb7caba16665
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

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