Sodium borohydride → 3-(1,3-Thiazol-4-yl)propan-1-ol

HRID 1096812ノート

反応式

HRID 1096812 の反応式
[BH4-].[Na+].[S:3]1[CH:7]=[C:6]([CH2:8][CH2:9][CH:10]=[O:11])[N:5]=[CH:4]1>CO>[S:3]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[N:5]=[CH:4]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 451216853-(1,3-Thiazol-4-yl)propanal

生成物 1

HCID 147742743-(1,3-Thiazol-4-yl)propan-1-ol収率 95.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

NaBH4 (1.68 g, 44.4 mmol) was added to a sol. of 3-thiazol-4-yl-propionaldehyde (4.35 g, 29.3 mmol) in MeOH (80 mL) at 0° C. The mixture was stirred for 30 min at 0° C., then for 1 h at rt. The mixture was cooled to 0° C., and ice was added. The mixture was partially evaporated under reduced pressure, and the residue was diluted with EtOAc. This mixture was washed with water and brine. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:1→EtOAc→CH2Cl2/EtOAc 1:9) yielded the title compound (4.01 g, 93%). LC-MS: tR=0.34, ES+: 144.16.

後処理

  1. waitfor 1 h at rt
  2. temperatureThe mixture was cooled to 0° C.
  3. additionice was added
  4. customThe mixture was partially evaporated under reduced pressure
  5. additionthe residue was diluted with EtOAc
  6. washThis mixture was washed with water and brine
  7. dry with materialextracts were dried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customPurification of the residue by FC (EtOAc/heptane 1:1→EtOAc→CH2Cl2/EtOAc 1:9)

出典と根拠

ORDレコード
ord-ac05362e60d4419faaf349337e89f67e
出典データセット
uspto-grants-2012_03
特許番号
US08138340B2

反応ノート

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