HCID 14219918、化合物 → Methyl 4-(2-hydroxyethyl)phenylacetate

HRID 1587878ノート

反応式

HRID 1587878 の反応式
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](O)=[O:14])=[CH:8][CH:7]=1)=[O:4]>O1CCCC1.C(OCC)(=O)C>[OH:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:7][CH:8]=1

参加物

4

反応物 1

HCID 14219918HCID 14219918、化合物

生成物 1

HCID 19088515Methyl 4-(2-hydroxyethyl)phenylacetate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Borane-tetrahydrofuran complex (40 ml of a 1.0 molar solution in tetrahydrofuran) was added, dropwise over 10 minutes, to a solution of 4-(methoxycarbonylmethyl)phenylacetic acid (see U.S. Pat. No. 3,341,531) (7.7 g) in tetrahydrofuran (100 ml) at 0°. The mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction was quenched by the addition of 2M hydrochloric acid (50 ml) then concentrated in vacuo. The residue was partitioned between dichloromethane (200 ml) and 2M hydrochloric acid (100 ml), the layers separated, and the aqueous layer extracted with dichloromethane (2×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was dissolved in ethyl acetate (100 ml) and the solution extracted with saturated aqueous sodium bicarbonate (2×100 ml). The aqueous extracts were combined, acidified with 2M hydrochloric acid (pH5) and extracted with dichloromethane (2×100 ml). The combined dichloromethane extracts were dried (MgSO4 ) and concentrated in vacuo to give the title compound as an oil, yield 2.7 g.

後処理

  1. customat 0°
  2. customThe reaction was quenched by the addition of 2M hydrochloric acid (50 ml)
  3. concentrationthen concentrated in vacuo
  4. customThe residue was partitioned between dichloromethane (200 ml) and 2M hydrochloric acid (100 ml)
  5. customthe layers separated
  6. extractionthe aqueous layer extracted with dichloromethane (2×50 ml)
  7. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give an oil which
  10. extractionthe solution extracted with saturated aqueous sodium bicarbonate (2×100 ml)
  11. extractionextracted with dichloromethane (2×100 ml)
  12. dry with materialThe combined dichloromethane extracts were dried (MgSO4 )
  13. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bc2d2cc9ab8048df858fd265f657699c
出典データセット
uspto-grants-1993_06
特許番号
US05219871

反応ノート

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