Acetone → (2R)-3,4-Dihydro-2H-1-benzopyran-2-methanol

HRID 23330ノート

反応式

HRID 23330 の反応式
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([OH:10])[CH3:9].[BH4-].[Na+].Cl.C[C:15](=[O:17])C>O>[O:10]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH2:7][CH2:9][C@@H:8]1[CH2:15][OH:17]

参加物

7

反応物 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 702EthanolHCID 1140TolueneHCID 4311764Sodium borohydride

生成物 1

HCID 7170029(2R)-3,4-Dihydro-2H-1-benzopyran-2-methanol

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of toluene (1000 ml) and ethanol (absolute, 520 ml) was stirred. Sodium borohydride (2.13 mol) was added at room temperature, under an inert atmosphere. The mixture was heated to 50° C. Intermediate (2) (2.14 mol) was added dropwise at 50° C. in a 90-minutes period (exothermic temperature rise of 15° C.; cooling required). The reaction mixture was stirred for 90 minutes at 50° C. Water (1500 ml) was added while stirring. Then, 2-propanone (100 ml) was added dropwise under slight cooling. The mixture was decomposed with HCl (180 ml). The organic layer was separated, dried, filtered and the solvent evaporated, yielding 295 g of (−)-(R)-3,4-dihydro-2H-1-benzopyran-2-methanol (interm. 3).

後処理

  1. temperature(exothermic temperature rise of 15° C.; cooling required)
  2. stirringThe reaction mixture was stirred for 90 minutes at 50° C
  3. stirringwhile stirring
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated

出典と根拠

ORDレコード
ord-938e808cf9014a2ebe3a8bf8550e251e
出典データセット
uspto-grants-2005_02
特許番号
US06852714B2

反応ノート

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