Acetic Acid → HCID 19000643, compound

HRID 2260393Notes

Reaction equation

HRID 2260393 reaction equation
[C:1]1([S:7][CH:8](S(C2C=CC=CC=2)(=NC)=O)[C:9](O)([C:11]2[CH2:15][CH2:14][CH2:13][CH:12]=2)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C(O)(=O)C>C1COCC1>[C:11]1([C:9]([CH2:8][S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH2:10])[CH2:15][CH2:14][CH2:13][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 19000708HCID 19000708, compound

Product 1

HCID 19000643HCID 19000643, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of S-[1-phenylthio-2-hydroxy-2-(cyclopent-1-enyl)propyl]-N-methyl-S-phenylsulfoximine (1.05 g, 2.7 mmol) in a mixture of THF (20 mL), H2O (8 mL) and acetic acid (8 mL) is added freshly prepared Al/Hg (1.3 g) in an ice-bath. After stirring at 0° C. for 5 hours, the mixture is filtered through a pad of Celite and the Celite is washed with EtOH (10 mL). The filtrate is concentrated in vacuo to ca. 5 mL. The residue is diluted with H2O (100 mL) and extracted with pentane (40 mL×5). The combined extracts are dried (Na2SO4), and evaporated in vacuo to dryness. The residue is chromatographed over a silica gel column (2×40 cm) using pentane as the eluent. The product is obtained as a syrup, 486 mg (83%). 1H NMR (CDCl3): δ1.73-2.08 (2H, m, CH2 -4), 2.49 (4H, t, J=6.72 Hz, CH2 -3 and -5), 3.78 (2H, s, CH2 --S), 5.01 (2H, d, J=6.86 Hz, CH2 =), 5.90 (1H, brs, CH=), 7.11-7.53 (5H, m, pH).

Workup

  1. additionis added freshly prepared Al/Hg (1.3 g) in an ice-bath
  2. filtrationthe mixture is filtered through a pad of Celite
  3. washthe Celite is washed with EtOH (10 mL)
  4. concentrationThe filtrate is concentrated in vacuo to ca. 5 mL
  5. additionThe residue is diluted with H2O (100 mL)
  6. extractionextracted with pentane (40 mL×5)
  7. dry with materialThe combined extracts are dried (Na2SO4)
  8. customevaporated in vacuo to dryness
  9. customThe residue is chromatographed over a silica gel column (2×40 cm)
  10. customThe product is obtained as a syrup, 486 mg (83%)

Sources & evidence

ORD record
ord-7e0ce091d3744b5992734612c2d996a5
Source dataset
uspto-grants-1995_12
Patent number
US05476952

Reaction notes

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