Acetic Anhydride → HCID 57771451, compound

HRID 2070611Notes

Reaction equation

HRID 2070611 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][CH2:12][CH2:11][CH2:10][C:7]2([CH2:9][CH2:8]2)[CH:6]1[OH:14])=[O:4].C(N(CC)CC)C.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]([CH:5]1[CH2:13][CH2:12][CH2:11][CH2:10][C:7]2([CH2:9][CH2:8]2)[CH:6]1[O:14][C:22](=[O:24])[CH3:23])=[O:4]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 57771416HCID 57771416, compound

Product 1

HCID 57771451HCID 57771451, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 4-hydroxy-spiro[2.6]nonane-5-carboxylic acid methyl ester (0.899 g) obtained in Step 2 in chloroform (18 mL) were added successively triethylamine (6.33 mL), 4-dimethylaminopyridine (0.11 g) and acetic anhydride (2.15 mL) under argon atmosphere and ice-cooling, followed by stirring the mixture at room temperature for 3.5 hours. After ice-cooling the reaction mixture and adding saturated aqueous sodium bicarbonate solution thereto, the reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (diethyl ether:hexane (volume ratio)=1:9) to give 4-acetoxy-spiro[2.6]nonane-5-carboxylic acid methyl ester (1.06 g).

Workup

  1. temperatureice-cooling
  2. temperatureAfter ice-cooling the reaction mixture
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (diethyl ether:hexane (volume ratio)=1:9)

Sources & evidence

ORD record
ord-e05737dd999a4e68ae053f751fcd6b1f
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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