Sodium Hydroxide → ((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

HRID 2365972ノート

反応式

HRID 2365972 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C(=O)C)=[C:11]([O:19][CH2:20][C@H:21]2[CH2:23][O:22]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][C@@H:21]([CH2:23][OH:22])[CH2:20][O:19][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 86644714Acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

生成物 1

HCID 66726995((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester (1.34 g, 4.26 mmol) in THF (30 ml), was added aq 2 M NaOH (2.45 ml). The mixture was stirred overnight at RT, THF was removed under reduced pressure and water (50 ml) was added. The water solution was then extracted three times with EtOAc and the combined extracts washed with water and brine. The organic layer was dried (Na2SO4), and evaporated in vacuo. The crude product (1.07 g) was used without purification.

後処理

  1. customTHF was removed under reduced pressure and water (50 ml)
  2. additionwas added
  3. extractionThe water solution was then extracted three times with EtOAc
  4. washthe combined extracts washed with water and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe crude product (1.07 g) was used without purification

出典と根拠

ORDレコード
ord-88ff4682aa16416699902981fd0e2edc
出典データセット
uspto-grants-2014_04
特許番号
US08697723B2

反応ノート

読み込み中…