Dimethyl Sulfoxide → HCID 21758989, compound

HRID 2211396Notes

Reaction equation

HRID 2211396 reaction equation
O[C:2]1[CH:7]=[CH:6]C=C[C:3]=1[CH:8]1[O:12]CC[O:9]1.CS(C)=O.[CH2:17]([C:19]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:27]([O:37]C(=O)C)=[CH:26][C:20]=1[O:21][CH2:22][CH2:23][CH2:24]I)[CH3:18].P([O-])([O-])([O-])=O.[CH2:46]1[CH2:50][O:49][CH2:48][CH2:47]1>>[CH2:17]([C:19]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)[C:27]([OH:37])=[CH:26][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][O:49][C:48]1[CH:47]=[CH:46][CH:50]=[CH:6][C:7]=1/[CH:2]=[CH:3]/[C:8]([OH:12])=[O:9])[CH3:18]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1061PhosphateHCID 8028Tetrahydrofuran2×HCID 2711182-(1,3-Dioxolan-2-yl)phenolHCID 19375866HCID 19375866, compound

Product 1

HCID 21758989HCID 21758989, compound

Procedure

60% Sodium hydride in oil was washed with hexane and suspended in dry DMSO (50 mL) with stirring under nitrogen. 2-(2-Hydroxyphenyl)-1,3-dioxolane (166 mg, 1 mmol) was dissolved in dry THF (10 mL) and added to the DMSO solution to give a pale yellow solution. After 20 minutes at room temperature 3-(2-ethyl-4-(4-fluorophenyl)-5-acetoxyphenoxy)propyl iodide (442 mg, 1 mmol) was added as a solution in dry THF (10 mL). After a further 2 hours at room temperature the reaction mixture was poured into pH 7.0 phosphate buffer and the mixture extracted 5 times with ether. The combined ether extracts were washed with water, dried with magnesium sulfate and evaporated to an oil which was chromatographed on a silica gel column eluting with ether/hexane (1:1). The title compound was isolated as an oil which was shown by the NMR spectrum to be contaminated with the starting phenol and a byproduct produced by loss of the acetyl group and alkylation produced with the starting iodide. These impurities could not be conveniently separated at this stage and the partially purified material was taken on to the next step.

Workup

  1. wash60% Sodium hydride in oil was washed with hexane
  2. customto give a pale yellow solution
  3. extractionthe mixture extracted 5 times with ether
  4. washThe combined ether extracts were washed with water
  5. dry with materialdried with magnesium sulfate
  6. customevaporated to an oil which
  7. customwas chromatographed on a silica gel column
  8. washeluting with ether/hexane (1:1)

Sources & evidence

ORD record
ord-cafd0b9535e046db82dc6551c65da653
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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