HCID 18920867, compound → HCID 18920865, compound

HRID 1289387Notes

Reaction equation

HRID 1289387 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][O:46]CC1C=CC=CC=1)[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[F:39])=[CH:28][CH:27]=1)=[O:17])C1C=CC=CC=1>[Pd].O1CCCC1>[OH:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[F:39])=[CH:28][CH:27]=1)=[O:17]

Participants

4

Reactant 1

HCID 18920867HCID 18920867, compound

Product 1

HCID 18920865HCID 18920865, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

First, 4 g of 6-[2,3-difluorobiphenyl-4'-yl]oxyhexyl 2,2-bis(6-benzyloxyhexyl)acetate, 1.3 g of 10% Pd-C, and 150 ml of tetrahydrofuran were placed in a 300 ml autoclave. The mixture was stirred at room temperature for 2 days under a hydrogen pressure of 10 kg/cm2. The catalyst was filtered away and a filtrate was concentrated. Thereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=2/3) to obtain 2.6 g of 6-[2,3-difluorobiphenyl-4'-yl]oxyhexyl 2,2-bis(6-hydroxyhexyl)acetate (Y: 90%). The compound thus obtained had a purity of 99.3% by HPLC.

Workup

  1. filtrationThe catalyst was filtered away
  2. concentrationa filtrate was concentrated
  3. customThereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-760b72e9bf9a44449465e9f2187a061e
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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