Acetic Anhydride → HCID 68724588, compound

HRID 1471409Notes

Reaction equation

HRID 1471409 reaction equation
O[CH:2]([CH3:17])[CH2:3][C:4]([CH:6]1[C:15](=[CH2:16])[CH:14]=[CH:13][CH2:12][C:7]21[CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:5].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>C([O-])(O)=O.[Na+]>[CH2:16]=[C:15]1[CH:14]=[CH:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]1[C:4](=[O:5])/[CH:3]=[CH:2]/[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium Acetate2×HCID 68725455HCID 68725455, compound

Product 1

HCID 68724588HCID 68724588, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-hydroxy-1-(7-methylenespiro[4.5]dec-8-en-6-yl)butan-1-one (0.65 mg, 2.77 mmol, 3:1 diastereomeric mixture), acetic anhydride (0.55 ml, 5.8 mmol) and sodium acetate (0.25 g, 3.0 mmol) was stirred at 80° C. for 7 h, treated with sodium acetate (0.1 g, 1.2 mmol), stirred at 80° C. for 7 h, cooled to 0° C., poured into cold saturated aqueous NaHCO3 (20 ml), and extracted three times with MTBE (10 ml). The combined organic phases were washed with a saturated aqueous solution of NaCl, dried (MgSO4), and concentrated. FC (30 g SiO2, hexane/MTBE 40:1) of the crude product (0.49 g) gave (E)-1-(7-methylenespiro[4.5]dec-8-en-6-yl)but-2-en-1-one (0.34 g, 57%). Boiling point: 100° C. (0.07 mbar).

Workup

  1. stirringstirred at 80° C. for 7 h
  2. temperaturecooled to 0° C.
  3. extractionextracted three times with MTBE (10 ml)
  4. washThe combined organic phases were washed with a saturated aqueous solution of NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0c756893b4fc41e79dda895d29cd9026
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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