Dimethyl Sulfoxide → HCID 10740642, compound

HRID 1781550Notes

Reaction equation

HRID 1781550 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.CS(C)=O.[Si:18]([O:25][C:26]1[C:34]([CH2:35][CH:36]([C:38]2[CH2:42][CH2:41][CH2:40][CH:39]=2)[OH:37])=[C:33]([O:43][CH3:44])[C:32]([CH3:45])=[C:31]2[C:27]=1[C:28](=[O:46])[O:29][CH2:30]2)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C>C(Cl)Cl>[C:38]1([C:36]([CH2:35][C:34]2[C:26]([O:25][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[C:27]3[C:31](=[C:32]([CH3:45])[C:33]=2[O:43][CH3:44])[CH2:30][O:29][C:28]3=[O:46])=[O:37])[CH2:42][CH2:41][CH2:40][CH:39]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 19046306HCID 19046306, compound

Product 1

HCID 10740642HCID 10740642, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-40 °C

Procedure

Trifluoroacetic anhydride (1.6 ml) in methylene chloride (3.6 ml) was added dropwise to dimethyl sulfoxide (1.05 ml) and CH2Cl2 (7.5 ml) under nitrogen over 5 minutes at -60° C. and stirred for 30 minutes. After addition of (±)-2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-1-cyclopentenyl-1-hydroxyethane (2 g) in methylene chloride (6 ml) over 15 minutes, the mixture was warmed to -40° C. over 1 hour. Triethylamine (10 ml) was added at -70° C., the cooling bath was removed, and after reaching ambient temperature the solution was diluted with ethyl acetate, washed twice with saturated aqueous potassium dihydrogen phosphate, brine, dried and evaporated. The solid residue was chromatographed on silica gel with 7:1 hexane, eluting with ethyl acetate to afford cyclopentenyl (4-tert-butyldimethylsilyloxy-1,3-dihydro -6-methoxy-7-methyl-3-oxoisobenzofuran-5-ylmethyl)methanone (1.65 g).

Workup

  1. customthe cooling bath was removed
  2. customafter reaching ambient temperature
  3. additionwas diluted with ethyl acetate
  4. washwashed twice with saturated aqueous potassium dihydrogen phosphate, brine
  5. customdried
  6. customevaporated
  7. customThe solid residue was chromatographed on silica gel with 7:1 hexane
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a413010b44c54d4998306c0743d3f4dd
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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