Dimethyl Sulfoxide → HCID 11008421, compound

HRID 1727311Notes

Reaction equation

HRID 1727311 reaction equation
CC([O-])(C)C.[K+].CS(C)=O.[CH2:11]([O:18][CH2:19][C@@H:20]1[CH2:23][C@H:22](C2C=C(C)C=CC=2S([O-])(=O)=O)[CH2:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CCOCC>[CH2:11]([O:18][CH2:19][CH:20]1[CH2:23][CH:22]=[CH:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 178427766HCID 178427766, compound

Product 1

HCID 11008421HCID 11008421, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 250 mL flask with t-BuOK (11.95 g, 0.11 mol) inside, dry DMSO 50 mL was added under argon to give a colorless solution. Then at room temperature, cis-3-(benzyloxymethyl)cyclobutyl-tosylate (12.3 g, 35.5 mmol) was added very slowly to the previous flask. The reaction mixture was left stirring at room temperature for 4 hr, after which time quench the reaction by adding H2O 200 mL slowly, followed by the addition of 100 mL Et2O. The separated water phase was re-extracted with Et2O three times and the combined organic phase was washed with H2O four times. The organic phase was dried over MgSO4 and concentrated to dryness to give a light yellow oil which was purified by silica gel flash chromatography (Hexane:EtOAc=9:1) to give 4.45 g (71.9%, Rf=0.59 ((Hexane: EtOAc=9:1)) the desired product. 1H NMR (CDCl3, 600 MHz): δ 2.19-2.21 (d, J=12, 1H), 2.66-2.69 (dd, J=13.2, 4.2, 1H), 3.11-3.14 (m, 1H), 3.50-3.56 (m, 2H), 4.54 (s, 2H), 6.09-6.11 (m, 2H), 7.27-7.35 (m, 5H). 13C NMR (CDCl3, 150 MHz): δ 34.40, 43.72, 73.32, 74.07, 127.75, 127.89, 128.59, 137.16, 138.59. IR (neat) νmax 3257, 2917, 2849, 1739, 1462, 1376, 1241, 967, 746.

Workup

  1. customto give a colorless solution
  2. waitThe reaction mixture was left
  3. customafter which time quench
  4. customthe reaction
  5. extractionThe separated water phase was re-extracted with Et2O three times
  6. washthe combined organic phase was washed with H2O four times
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated to dryness
  9. customto give a light yellow oil which
  10. customwas purified by silica gel flash chromatography (Hexane:EtOAc=9:1)

Sources & evidence

ORD record
ord-1d9ec76bfe2948b4aaf8b0dc4859555f
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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