1-(2,3,4-Trifluorophenyl)hept-1-YN-3-OL → 1-(3-Hydroxyheptyl)-2,3,4-trifluorobenzene

HRID 1765005Notes

Reaction equation

HRID 1765005 reaction equation
[OH:1][CH:2]([CH2:14][CH2:15][CH2:16][CH3:17])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[C:6]=1[F:13].[H][H]>C(OCC)(=O)C.[C].[Pd]>[OH:1][CH:2]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[C:6]=1[F:13]

Participants

5

Reactant 2

HCID 231157251-(2,3,4-Trifluorophenyl)hept-1-YN-3-OLHCID 178418361HCID 178418361, compound

Product 1

HCID 231157181-(3-Hydroxyheptyl)-2,3,4-trifluorobenzeneYield 91.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In 730 mL of ethyl acetate, 183 g of 1-(3-hydroxy-1-heptynyl)-2,3,4-trifluorobenzene was dissolved, and 9 g of 5% palladium carbon (50% in water) was added. Then, the mixutre was stirred for 6 hours at a hydrogen pressure of 0.4 MPa. After the catalyst was removed by filtration (using cellulose), the solvent was evaporated under a reduced pressure to obtain 170 g of 1-(3-hydroxyheptyl)-2,3,4-trifluorobenzene as a light yellow solid.

Workup

  1. customAfter the catalyst was removed by filtration (using cellulose)
  2. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-ea2e57cf8f9b412fb83cb5050f59903e
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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