Acetone → HCID 13325399, compound

HRID 1262957Notes

Reaction equation

HRID 1262957 reaction equation
CC(C)=O.C(Br)CCCCCC.C(=O)([O-])[O-].[K+].[K+].C([O:22][C@@H:23]1[C@@H:36]([O:37]C(=O)C)[C@H:35]([O:41]C(=O)C)[CH2:34][O:33][C@H:24]1[S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=O)C>C(O)(=O)C>[S:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C@@H:24]1[O:33][CH2:34][C@@H:35]([OH:41])[C@H:36]([OH:37])[C@H:23]1[OH:22]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 13325464HCID 13325464, compound

Product 1

HCID 13325399HCID 13325399, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 20 ml. of a 50% aqueous acetone solution were added 2.92 g. of 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (17) and 1.79 g. of n-heptyl bromide. To the solution was further added 1.38 g. of potassium carbonate and then a boiling under reflux was carried out for one hour. After completion of the reaction, the solution was neutralized with acetic acid, extracted with chloroform washed with water, and dried. The used solvent was distilled away to obtain 2.55 g. of colorless oily n-heptyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (18). The yield was 65.3%.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with chloroform
  3. washwashed with water
  4. customdried
  5. distillationThe used solvent was distilled away
  6. customto obtain 2.55 g

Sources & evidence

ORD record
ord-9728c824601d4859bcd0438fff4bcfdf
Source dataset
uspto-grants-1984_06
Patent number
US04454123

Reaction notes

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