Acetic Anhydride → HCID 86647587, compound

HRID 1471404Notes

Reaction equation

HRID 1471404 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])[CH3:13])[C:4]([CH3:15])=[CH:3]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])(=O)C.[Na+]>[OH-].[Na+]>[C:16]([O:1][C@H:2]1[CH:3]=[C:4]([CH3:15])[C@H:5]([C:12](=[O:14])[CH3:13])[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:11]1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 68773753HCID 68773753, compound

Product 1

HCID 86647587HCID 86647587, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8:92 cis/trans-1-(9-hydroxy-7-methylspiro[4.5]dec-7-en-6-yl)ethanone (4.2 g, 20.2 mmol) was treated with acetic anhydride (4 ml, 42.3 mmol) and sodium acetate (1.65 g, 20.2 mmol). The resulting mixture was stirred at 80° C. for 1 h, poured into cold 2N aqueous NaOH (50 ml), and extracted twice with MTBE (40 ml). The combined organic phases were washed with water (40 ml), with a saturated aqueous solution of NaCl (40 ml), dried (MgSO4), and concentrated. FC (300 g SiO2, hexane/MTBE 8:1) of the crude product (4.82 g) gave 8:92 cis/trans-10-acetyl-9-methylspiro[4.5]dec-8-en-7-yl acetate (4.1 g, 82%).

Workup

  1. extractionextracted twice with MTBE (40 ml)
  2. washThe combined organic phases were washed with water (40 ml), with a saturated aqueous solution of NaCl (40 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c07c44ff01c44a268cf31cabc1110725
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

Loading…