Hexane → HCID 9805015, compound

HRID 975181Notes

Reaction equation

HRID 975181 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:42])[C:15]([O:17][CH2:18][CH2:19][C:20]2([CH3:41])[O:25][C:24]3[C:26]([CH3:40])=[C:27]([CH3:39])[C:28]([O:31]CC4C=CC=CC=4)=[C:29]([CH3:30])[C:23]=3[CH2:22][CH2:21]2)=[O:16])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCCCCC>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:42])[C:15]([O:17][CH2:18][CH2:19][C:20]2([CH3:41])[O:25][C:24]3[C:26]([CH3:40])=[C:27]([CH3:39])[C:28]([OH:31])=[C:29]([CH3:30])[C:23]=3[CH2:22][CH2:21]2)=[O:16])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 8058HexaneHCID 18973233HCID 18973233, compound

Product 1

HCID 9805015HCID 9805015, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2yl)ethyl 2-(3-fluoro4-phenyl-phenyl)propionate in ethyl acetate was treated with 10% palladium on charcoal (Aldrich, 0.5 g). The resulting mixture was hydrogenated on a Parr Apparatus [initial pressure 60 pounds/inch2 (psi)]. After 18 hours, the reaction mixture was filtered, and the resulting solution concentrated in vacuo. The residue was subjected to flash chromatography (silica gel, 2:8, v:v, ethyl acetate:hexane). Concentration of the appropriate fractions afforded a clear oil. Hexane was added to the oil and a white solid formed upon standing. The white solid was collected by filtration to afford 0.91 g (36% yield) of 2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2yl)ethyl 2-(3-fluoro4-phenyl-phenyl)propionate as a mixture of stereoisomers.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe resulting solution concentrated in vacuo
  3. customConcentration of the appropriate fractions afforded a clear oil
  4. customa white solid formed
  5. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-ab2b97afc82c466fa36033841e166bd2
Source dataset
uspto-grants-1997_03
Patent number
US05607966

Reaction notes

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