Acetic Anhydride → HCID 20077664, compound

HRID 2226647Notes

Reaction equation

HRID 2226647 reaction equation
[CH3:1][C:2]([OH:20])([CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:3]#[C:4][CH2:5][CH:6]([OH:8])[CH3:7].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:8][CH:6]([CH2:5][C:4]#[C:3][C:2]([CH3:1])([OH:20])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH3:7])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11022377HCID 11022377, compound

Product 1

HCID 20077664HCID 20077664, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 230 mg (0.814 mmole) of 6,10,14-trimethyl-4-pentadecyne-2,6-diol (produced in accordance with Example XVI) and 0.25 mL (2.65 mmoles) of acetic anhydride in 0.25 mL of pyridine (A.C.S. reagent-grade, purchased from Aldrich Chemical Co., Milwaukee, Wis.) was stirred, while being maintained under a nitrogen atmosphere, at room temperature for 8 hours. After destroying excess acetic anhydride by addition of 10 mL of ice-cold 1M aqueous sodium hydroxide, the mixture was diluted with 20 mL of hexane and 25 mL of 10% aqueous sodium chloride. The layers were then separated, and the organic layer washed in successive order with 1:1 (v/v) 1M aqueous sodium hydroxide: 10% aqueous sodium chloride (1×10 mL), 1:1 (v/v) 2M aqueous hydrochloric acid: saturated brine (2×20 mL), saturated aqueous sodium bicarbonate (1×10 mL), and saturated brine (1×10 mL). The washed organic layer was subsequently dried over anhydrous magnesium sulfate and filtered. Removal of the volatile organic material by evaporation at reduced pressure afforded 249 mg (94% yield) of 2-acetoxy-6,10,14-trimethyl-4-pentadecyn-6-ol (i.e., the product derived by selective acetylation of the 2° alcohol functionality in the starting alkynediol).

Workup

  1. customAfter destroying excess acetic anhydride
  2. additionby addition of 10 mL of ice-cold 1M aqueous sodium hydroxide
  3. additionthe mixture was diluted with 20 mL of hexane and 25 mL of 10% aqueous sodium chloride
  4. customThe layers were then separated
  5. washthe organic layer washed in successive order with 1:1 (v/v) 1M aqueous sodium hydroxide
  6. dry with materialThe washed organic layer was subsequently dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customRemoval of the volatile organic material
  9. customby evaporation at reduced pressure

Sources & evidence

ORD record
ord-5db2fe18b5ab41d28a4e00589bbc6f4a
Source dataset
uspto-grants-1994_09
Patent number
US05349071

Reaction notes

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