(2R)-Octan-2-yl 4-(benzyloxy)-3-fluorobenzoate → (R)-(-)-1-Methylheptyl 4-Hydroxy-3-fluorobenzoate

HRID 433046Notes

Reaction equation

HRID 433046 reaction equation
C([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([O:15][C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:14])=[CH:11][C:10]=1[F:26])C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([O:15][C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:14])=[CH:11][C:10]=1[F:26]

Participants

4

Reactant 1

HCID 70010782(2R)-Octan-2-yl 4-(benzyloxy)-3-fluorobenzoate

Product 1

HCID 54392229(R)-(-)-1-Methylheptyl 4-Hydroxy-3-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on charcoal (0.3 g), was added to a solution of compound 12 (10.0 g, 28 mmol) in ethyl acetate (300 ml). The solution was evacuated and left stirring with hydrogen at atmospheric pressure for 24 h. The catalyst was filtered off and the solvent removed in vacuo to yield a yellow oil which was purified by column chromatography (dichloromethane) on silica to yield the pure colourless oil. Yield 5.8 g (77%). [α]D=−33.7° at 25° C.

Workup

  1. customThe solution was evacuated
  2. waitleft
  3. filtrationThe catalyst was filtered off
  4. customthe solvent removed in vacuo
  5. customto yield a yellow oil which
  6. customwas purified by column chromatography (dichloromethane) on silica
  7. customto yield the pure colourless oil
  8. customat 25° C.

Sources & evidence

ORD record
ord-e5569b93976c42d59548fc47991d1568
Source dataset
uspto-grants-2003_12
Patent number
US06666989B1

Reaction notes

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