Acetic Anhydride → HCID 131732748, compound

HRID 1471394Notes

Reaction equation

HRID 1471394 reaction equation
[OH:1][C@@H:2]1[CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[C@@H:5]([C:12]([O:14][CH3:15])=[O:13])[C:4]([CH3:16])=[CH:3]1.[C:17](OC(=O)C)(=[O:19])[CH3:18].C([O-])(=O)C.[Na+]>[OH-].[Na+]>[C:17]([O:1][C@@H:2]1[CH2:11][C:6]2([CH2:7][CH2:8][CH2:9][CH2:10]2)[C@@H:5]([C:12]([O:14][CH3:15])=[O:13])[C:4]([CH3:16])=[CH:3]1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 131732747HCID 131732747, compound

Product 1

HCID 131732748HCID 131732748, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A part of the crude trans-methyl 9-hydroxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate obtained (4.0 g) was treated with acetic anhydride (3.5 ml, 37.4 mmol) and sodium acetate (1.46 g, 17.8 mmol). The resulting mixture was stirred at 80° C. for 4 h, poured into cold 2N aqueous NaOH (20 ml), and extracted twice with MTBE (30 ml). The combined organic phases were washed with water (30 ml), with a saturated aqueous solution of NaCl (30 ml), dried (MgSO4), concentrated giving crude trans-methyl 9-acetoxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (4.4 g, 92%).

Workup

  1. extractionextracted twice with MTBE (30 ml)
  2. washThe combined organic phases were washed with water (30 ml), with a saturated aqueous solution of NaCl (30 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-06d3009681454879998f427b464f9e63
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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