Acetone → HCID 52919351, compound

HRID 1045082Notes

Reaction equation

HRID 1045082 reaction equation
[C:1]1([S:7]([CH:10]([CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH:28][CH2:29][CH:30]=[CH:31][CH2:32][CH:33]=[CH:34][CH2:35][CH:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=[O:45]>>[C:1]1([S:7]([CH:10]([CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:45])=[O:22])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 180AcetoneHCID 67171474HCID 67171474, compound

Product 1

HCID 52919351HCID 52919351, compoundYield 84%

Procedure

Jone's reagent was added dropwise to a stirred solution of 17Z,20Z,23Z,26Z)-12-(phenylsulfonyl)dotriaconta-17,20,23,26-tetraen-1-ol (1 M solution in THF, 0.764 mL, 0.764 mmol) dissolved in acetone (5 mL) till the completion of reaction (TLC monitoring). The reaction was quenched with methanol (2 mL) and stirred for 30 min. The solvent was then removed and the crude was purified by silica gel column chromatography using 30% ethyl acetate/hexane to furnish the title compound as a clear oil (0.0643, 84%). 1H NMR (CDCl3): δ7.88 (d, 2H, J=7.2 Hz), 7.60 (m, 3H), 5.36 (m, 8H), 2.79 (m, 7H), 2.27 (t, 2H, J=6.8 Hz), 2.07 (m, 4H), 1.68 (m, 2H), 1.37-1.20 (m, 28H), 1.04 (t, 3H, J=6.8 Hz). m/z (APCI) 613.45 (M++1).

Workup

  1. customThe reaction was quenched with methanol (2 mL)
  2. customThe solvent was then removed
  3. customthe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e4ad8c4d7e0242c38a9b187c5acd877b
Source dataset
uspto-grants-2013_10
Patent number
US08563760B2

Reaction notes

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