Dimethylformamide → 8-Chlorospiro[4.5]dec-7-ene-7-carbaldehyde

HRID 1035898Notes

Reaction equation

HRID 1035898 reaction equation
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)[Cl:8].[CH2:11]1[C:15]2([CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12]1>ClCCl>[Cl:8][C:18]1[CH2:19][CH2:20][C:15]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:16][C:17]=1[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 14626805Spiro(4.5)decan-8-one

Product 1

HCID 866481768-Chlorospiro[4.5]dec-7-ene-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dimethylformamide (2.81 mL) in dichloromethane (40 mL) was added dropwise POCl3 (2.78 mL) at 0° C. The reaction mixture was warmed up to room temperature and spiro[4.5]decan-8-one (3.95 g) in dichloromethane (5 mL) was added dropwise. The mixture was stirred overnight. The reaction was quenched with cold aqueous sodium acetate and the resulting mixture was extracted with ether and the organic layer was dried over Na2SO4, filtered, and concentrated to provide the title compound.

Workup

  1. customThe reaction was quenched with cold aqueous sodium acetate
  2. extractionthe resulting mixture was extracted with ether
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4dd2dbff20ed4cbd96beb4ce3f0216d8
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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