Ethanol → Ethyl 17-hydroxy-heptadecanoate

HRID 1367724Notes

Reaction equation

HRID 1367724 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.CCO>CCOC(C)=O>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66970149Ethyl 17-(tetrahydropyran-2-yl-oxy)-heptadecanoate

Product 1

HCID 21833404Ethyl 17-hydroxy-heptadecanoateYield 92.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 17-(tetrahydropyran-2-yl-oxy)-heptadecanoate 78 (365 mg, 0.916 mmol) and PPTS (12 mg, 0.046 mmol) were dissolved in abs. EtOH (6 ml) and the reaction mixture was stirred at 45° C. for 10 h. Reaction mixture was diluted with EtOAc and washed with H2O. The extract was dried over Na2SO4 and evaporated. The residue was purified by silica gel chromatography in hexane-EtOAc (95:5, 90:10) to yield the product 79 (266 mg, 92%).

Workup

  1. customReaction mixture
  2. washwashed with H2O
  3. dry with materialThe extract was dried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography in hexane-EtOAc (95:5, 90:10)

Sources & evidence

ORD record
ord-a16e4725d43b46aaa15933e71df7b602
Source dataset
uspto-grants-2011_02
Patent number
US07893286B2

Reaction notes

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