HCID 14219918, 화합물 → Methyl 4-(2-hydroxyethyl)phenylacetate

HRID 1463885노트

반응식

HRID 1463885 반응식
[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

참가 물질

4

반응물 1

HCID 14219918HCID 14219918, 화합물

생성물 1

HCID 19088515Methyl 4-(2-hydroxyethyl)phenylacetate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-70b4a2d0e1914fb094d5e8f82b9e9ddc
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05302595

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