Hydrochloric Acid → HCID 68724101, compound

HRID 1471405Notes

Reaction equation

HRID 1471405 reaction equation
C(O[C@H:5]1[CH:14]=[C:13]([CH3:15])[C@H:12]([C:16](=[O:18])[CH3:17])[C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6]1)(=O)C.Cl.[CH2:20]1CCN2C(=NCCC2)CC1>>[CH3:20][CH2:17][C:16]([C:12]1[C:7]2([CH2:6][CH:5]=[CH:14][C:13]=1[CH3:15])[CH2:8][CH2:9][CH2:10][CH2:11]2)=[O:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647587HCID 86647587, compound

Product 1

HCID 68724101HCID 68724101, compoundYield 72%

Procedure

A solution of 8:92 cis/trans-10-acetyl-9-methylspiro[4.5]dec-8-en-7-yl acetate (4.1 g, 16.4 mmol) in DBU (30 ml) was stirred for 19 h at 40° C. The reaction mixture was poured into cold 2N aqueous HCl (100 ml), and extracted twice with cyclohexane (50 ml). The combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (40 ml), dried (MgSO4), concentrated. FC (500 g SiO2, hexane/MTBE 50:1) of the crude product (2.92 g) gave methyl 1-(7-methylspiro[4.5]deca-6,8-dien-6-yl)ethanone (2.25 g, 72%).

Workup

  1. extractionextracted twice with cyclohexane (50 ml)
  2. washThe combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (40 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-85356ae80b544040bd4ffc2794d5fa4a
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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