Acetic Anhydride → HCID 14478577, compound

HRID 2072616Notes

Reaction equation

HRID 2072616 reaction equation
[OH:1][C@:2]([CH3:18])([C:16]#[CH:17])[CH2:3][CH2:4][C:5]1[C:6](=[O:15])[C:7]([CH3:14])=[C:8]([CH3:13])[C:9](=[O:12])[C:10]=1[CH3:11].[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(N(CC)CC)C>[C:19]([O:1][C@:2]([CH3:18])([C:16]#[CH:17])[CH2:3][CH2:4][C:5]1[C:6](=[O:15])[C:7]([CH3:14])=[C:8]([CH3:13])[C:9](=[O:12])[C:10]=1[CH3:11])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14478561HCID 14478561, compound

Product 1

HCID 14478577HCID 14478577, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1.23 g (5 mmol) of (S)-2-[3-hydroxy-3-methyl -4-pentynyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione ([α]D25 +11.3° CH2Cl2), 1.05 mL of triethylamine, 120 mg of 4-N,N-dimethylamino pyridine, and 0.6 mL of acetic anhydride in 8 mL of CH2CL2 was stirred at 25° C. under argon for 17 h. It was diluted with CH2CL2 (70 mL), washed with 1.0N HCl, saturated NaHCO3 solution, water and dried over MgSO4. The crude material (1.6 g) was purified by flash chromatography on silica gol (50 g; 230-400 mesh). Elution with ether:petroleum ether (3.17) gave 1.47 g of (S)-2-[3-(acetyloxy)-3-methyl-4-pentynyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione as a yellow oil, [α]D25 -21.42° (c, 0.994, CH2Cl2).

Workup

  1. additionIt was diluted with CH2CL2 (70 mL)
  2. washwashed with 1.0N HCl, saturated NaHCO3 solution, water
  3. dry with materialdried over MgSO4
  4. customThe crude material (1.6 g) was purified by flash chromatography on silica gol (50 g; 230-400 mesh)
  5. washElution with ether

Sources & evidence

ORD record
ord-d14da7aae73742d1909c12ac88510cab
Source dataset
uspto-grants-1990_04
Patent number
US04913851

Reaction notes

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