Acetic Anhydride → HCID 14478577, compound

HRID 1722210Notes

Reaction equation

HRID 1722210 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:petroleum ether (3:17)

Sources & evidence

ORD record
ord-a965467dc1e54ba5858b7defe5a7ec09
Source dataset
uspto-grants-1989_08
Patent number
US04855085

Reaction notes

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