HCID 71077124, compound → HCID 71077074, compound

HRID 2273373Notes

Reaction equation

HRID 2273373 reaction equation
[F:1][C:2]([F:32])([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])=[CH:21][CH:20]=1)[C:3]1[C:8]([F:9])=[CH:7][C:6]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[CH:5][C:4]=1[F:17]>C1COCC1>[F:32][C:2]([F:1])([O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])=[CH:23][CH:24]=1)[C:3]1[C:4]([F:17])=[CH:5][C:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[CH:7][C:8]=1[F:9]

Participants

3

Reactant 1

HCID 71077124HCID 71077124, compound

Product 1

HCID 71077074HCID 71077074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-{Difluoro[4-(6-hydroxyhex-1-ynyl)phenoxy]methyl}-3,5-difluorophenyl)-hex-5-yn-1-ol is hydrogenated to completion on palladium/active carbon catalyst in THF. The catalyst is filtered off, the solvent is removed in vacuo, and the crude product is chromatographed on silica gel with toluene/ethyl acetate (1:2), giving 6-(4-{difluoro[4-(6-hydroxyhexyl)-phenoxy]methyl}-3,5-difluorophenyl)hexan-1-ol as a colourless solid.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. customthe crude product is chromatographed on silica gel with toluene/ethyl acetate (1:2)

Sources & evidence

ORD record
ord-3eafe8111b4f44059e93f9ec80718935
Source dataset
uspto-grants-2015_09
Patent number
US09120969B2

Reaction notes

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