HCID 14219918, compound → HCID 19088515, compound

HRID 1463885Notes

Reaction equation

HRID 1463885 reaction equation
[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

Participants

4

Reactant 1

HCID 14219918HCID 14219918, compound

Product 1

HCID 19088515HCID 19088515, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-70b4a2d0e1914fb094d5e8f82b9e9ddc
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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