HCID 178525420, compound → HCID 178525421, compound

HRID 1289403Notes

Reaction equation

HRID 1289403 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52]CC1C=CC=CC=1)[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=2[F:45])[CH2:34][CH2:33]1)=[O:17])C1C=CC=CC=1>[Pd].O1CCCC1>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][OH:52])[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C@H:32]1[CH2:33][CH2:34][C@H:35]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=2[F:45])[CH2:36][CH2:37]1)=[O:17]

Participants

4

Reactant 1

HCID 178525420HCID 178525420, compound

Product 1

HCID 178525421HCID 178525421, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

First, 5.3 g of 13-[trans-4-(2,3-difluorophenyl)cyclohexyl]tridecyl 2,2-bis(6-benzyloxyhexyl)acetate, 1.7 g of 10% Pd-C, and 100 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. A catalyst was filtered away and a filtrate was concentrated. Thereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=7/3) to obtain 4.1 g of 13-[trans-4-(2,3-difluorophenyl)cyclohexyl]tridecyl 2,2-bis(6-hydroxyhexyl)acetate (Y: 98%). The compound thus obtained had a purity of 99% by HPLC.

Workup

  1. filtrationA catalyst was filtered away
  2. concentrationa filtrate was concentrated
  3. customThereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-ac6b27cdee7f4926ac1abb0a70577918
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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