Sulfuric Acid → HCID 21258641, compound

HRID 617603Notes

Reaction equation

HRID 617603 reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]([O:13][CH2:14][CH2:15][C:16]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(O)[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:36](#[N:38])[CH3:37]>>[CH2:6]([O:13][CH2:14][CH2:15][C:16]([NH:38][C:36](=[O:2])[CH3:37])([CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 22618832HCID 22618832, compound

Product 1

HCID 21258641HCID 21258641, compound

Procedure

Sulfuric acid (4.2 g) was added to a solution of 1,5-dibenzyloxy-3-(2-phenylethyl)-3-pentanol (5.8 g) in acetonitrile (50 ml) under ice-cooling and the mixture was stirred at room temperature for 3 hours. The mixture was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue obtained was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3) to give the subject compound (2.2 g) as a yellowish oily substance.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-5914c373f4164fa5bba58383a818d056
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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