Acetic Anhydride → HCID 14478577, compound

HRID 1199323Notes

Reaction equation

HRID 1199323 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 gel (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 gel (50 g; 230-400 mesh)
  5. washElution with ether:petroleum ether (3:17)

Sources & evidence

ORD record
ord-db49bfcd48764d9ca8a2cec85d6ca855
Source dataset
uspto-grants-1990_02
Patent number
US04900476

Reaction notes

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