Acetic Anhydride → HCID 68722435, compound
Reaction equation
O[CH:2]([CH3:17])[CH2:3][C:4]([CH:6]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:7]21[CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:5].OC(C)CC(C1C2(CC=CC=1C)CCCC2)=O.OC(C)CC(C1C(=C)C=CCC21CCCC2)=O.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>C([O-])(O)=O.[Na+]>[CH3:16][C:15]1[CH:6]([C:4](=[O:5])/[CH:3]=[CH:2]/[CH3:17])[C:7]2([CH:12]=[CH:13][CH:14]=1)[CH2:8][CH2:9][CH2:10][CH2:11]2Participants
Conditions
- Temperature
- 80 °C
Procedure
A 81:14:3 mixture of 3-hydroxy-1-(7-methylspiro[4.5]deca-7,9-dien-6-yl)butan-1-one, 3-hydroxy-1-(7-methylspiro[4.5]deca-6,8-dien-6-yl)butan-1-one, and 3-hydroxy-1-(7-methylenespiro[4.5]dec-8-en-6-yl)butan-1-one (0.2 g, 0.85 mmol), acetic anhydride (0.17 ml, 1.8 mmol) and sodium acetate (77 mg, 3.0 mmol) was stirred at 80° C. for 16 h, treated with sodium acetate (30 mg, 0.37 mmol), stirred at 80° C. for 2 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 twice with a saturated aqueous solution of NaCl, dried (MgSO4), and concentrated. FC (30 g SiO2, hexane/MTBE 60:1) of the crude product (0.2 g) gave (E)-1-(7-methylspiro[4.5]deca-7,9-dien-6-yl)but-2-en-1-one (0.139 g, 77%). Boiling point: 100° C. (0.07 mbar).
Workup
- stirringstirred at 80° C. for 2 h
- temperaturecooled to 0° C.
- extractionextracted three times with MTBE (10 ml)
- washThe combined organic phases were washed twice with a saturated aqueous solution of NaCl
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-663099d34cd04947ae56add22974b729
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012391B2
Reaction notes
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