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

HRID 706888Notes

Reaction equation

HRID 706888 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-d86c1274f77d43faaedcc29794392aca
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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