Water → HCID 86642708, compound

HRID 1361079Notes

Reaction equation

HRID 1361079 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=1)[CH2:2][CH2:3][CH3:4].[CH2:30]([S:34](Cl)(=[O:36])=[O:35])[CH2:31][CH2:32][CH3:33].C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[CH2:30]([S:34]([O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][C:11]2[CH:10]=[CH:9][C:8]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:7][C:6]=2[O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:16][C:17]=1[O:22][CH3:23])(=[O:36])=[O:35])[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 66971962HCID 66971962, compound

Product 1

HCID 86642708HCID 86642708, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 400 mg (1 mmol) of methyl 3-{3-butoxy-4-[3-(4-hydroxy-3-methoxyphenyl)propyl]phenyl}propanoate, 170 μl (1.3 mmol) of butanesulfonyl chloride and 250 μl of triethylamine in 10 ml of tetrahydrofuran is stirred for 12 hours at room temperature. After addition of water and extraction with ethyl acetate, the organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The residual oil is purified by chromatography on a column of silica eluted with an 8/2 heptane/ethyl acetate mixture. 410 mg of methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-3-butoxyphenyl)propanoate are obtained in the form of a yellow oil.

Workup

  1. washthe organic phases are washed with saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual oil is purified by chromatography on a column of silica
  6. washeluted with an 8/2 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-46556142b1b34cfca3ffc41d79a21a1d
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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