Isopropanol → HCID 22404408, compound

HRID 259923Notes

Reaction equation

HRID 259923 reaction equation
[C:1]([C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:14][C:15](=[O:17])[CH3:16])[CH2:7][CH2:8]C(OCC)=O)([O:3][CH2:4][CH3:5])=[O:2].[H-].[Na+].C([OH:28])(C)C>CN(C)C=O>[C:18]([C:6]1([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:7][C:8](=[O:28])[CH2:16][C:15](=[O:17])[CH2:14]1)([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 22404405HCID 22404405, compound

Product 1

HCID 22404408HCID 22404408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 14.3 g (0.047 mol) of ethyl 3,3-biscarbethoxy-5-oxo-hexanecarboxylate in 40 ml of dimethylformamide was added dropwise to a suspension of 3.6 g (0.118 mol) of 80 % strength by weight sodium hydride in 200 ml of dimethylformamide. After stirring at 20°-25° C. for about 15 hours, the reaction was stopped by adding 5 ml of isopropanol. The reaction products were partitioned between ethyl acetate and 1 molar hydrochloric acid. The organic phase was then separated, dried and evaporated down. Yield: 2.2 g of a crude product oil.

Workup

  1. customThe reaction products were partitioned between ethyl acetate and 1 molar hydrochloric acid
  2. customThe organic phase was then separated
  3. customdried
  4. customevaporated down

Sources & evidence

ORD record
ord-4fe31d85ec2c49d99a4dd73bd214758e
Source dataset
uspto-grants-1996_06
Patent number
US05523462

Reaction notes

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