HCID 52919351, compound → HCID 52919352, compound

HRID 1045083Notes

Reaction equation

HRID 1045083 reaction equation
C1(S([CH:10]([CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])(=O)=O)C=CC=CC=1>CO.C(OCC)(=O)C.CCCCCC.[Na].[Hg]>[C:21]([OH:23])(=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

5

Reactant 1

HCID 52919351HCID 52919351, compound

Product 1

HCID 52919352HCID 52919352, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 9837419Sodium amalgamCatalystHCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of (17Z,20Z,23Z,26Z)-12-(phenylsulfonyl)dotriaconta-17,20,23,26-tetraenoic acid (0.0643 g, 0.105 mmol) in methanol (8 mL) was added Na2HPO4 (0.074 g, 0.525 mmol) and 10% sodium amalgam (5.16 g, 2.308 mmol) and the resulting reaction mixture was stirred under nitrogen at room temperature for 40 h. The solvent was decanted and acidified (pH 4) with 1M HCl. The aqueous phase was extracted with DCM (3×10 mL), washed with brine (2×10 mL), dried over MgSO4, filtered and evaporated. The product from the crude was isolated by flash chromatography using 25% ethyl acetate/hexane as eluent to afford the title product as a light yellow oil (0.025 g, 51%). 1H NMR (CDCl3): δ 5.36 (m, 8H), 2.79 (m, 6H), 2.28 (t, 2H, J=6.7 Hz), 1.99 (m, 4H), 1.61 (m, 2H), 1.51-1.18 (m, 30H), 0.97 (t, 3H, J=6.8 Hz). m/z (APCI) 473.62 (M++1).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was decanted
  3. extractionThe aqueous phase was extracted with DCM (3×10 mL)
  4. washwashed with brine (2×10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product from the crude was isolated by flash chromatography

Sources & evidence

ORD record
ord-c4cbfcda0f244ea5ac5c8ee3914acb12
Source dataset
uspto-grants-2013_10
Patent number
US08563760B2

Reaction notes

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