Acetic Anhydride → HCID 19801099, compound

HRID 1646642Notes

Reaction equation

HRID 1646642 reaction equation
[O:1]1[CH:3]([CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[C:2]1([CH:10]1[CH:15]([O:16][CH3:17])[CH:14]([OH:18])[CH2:13][CH2:12][C:11]1([CH2:20][I:21])[OH:19])[CH3:9].CN(C1C=CC=CN=1)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClCCl.C(OCC)(=O)C>[C:31]([O:18][CH:14]1[CH2:13][CH2:12][C:11]([CH2:20][I:21])([OH:19])[CH:10]([C:2]2([CH3:9])[O:1][CH:3]2[CH2:4][CH:5]=[C:6]([CH3:7])[CH3:8])[CH:15]1[O:16][CH3:17])(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 19801041HCID 19801041, compound

Product 1

HCID 19801099HCID 19801099, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In dichloromethane (5 ml) was dissolved 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-iodomethyl-1,4-cyclohexanediol (2.08 g). To the solution were added dimethylaminopyridine (0.74 g) and acetic anhydride (0.58 ml). The mixture was stirred for 30 minutes. The reaction mixture was diluted with ethyl acetate (50 ml), which was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the solvent was purified by means of a silica gel column chromatography (carrier 100 g, developing solvent: ethyl acetate - hexane=1:3) to afford 4-O-acetyl-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-iodomethyl-3-methoxy-1,4-cyclohexanediol (2.19 g: yield 95%) as a colorless oily product.

Workup

  1. washwas washed with a saturated aqueous solution of sodium hydrogencarbonate
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe solvent was purified by means of a silica gel column chromatography (carrier 100 g, developing solvent: ethyl acetate - hexane=1:3)

Sources & evidence

ORD record
ord-07429a2818374e7da2ad08e8089a28c2
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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