Water → HCID 21474587, compound

HRID 1756421Notes

Reaction equation

HRID 1756421 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=[O:18])[C:15]([OH:17])=[O:16])[CH:5]=[CH:4][C:3]1=2.[CH2:20]1COCC1.C([Mg]I)C.O>C(OCC)C>[OH:18][C:14]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:19])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)([CH3:20])[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 12051800HCID 12051800, compoundHCID 178461634HCID 178461634, compound

Product 1

HCID 21474587HCID 21474587, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.1 g (12 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylic acid and 50 ml of THF are introduced into a three-necked flask. At 0° C. and under a stream of nitrogen, 16 ml (48 retool) of a solution of ethylmagnesium iodide in ethyl ether (3M) are added dropwise and the mixture is stirred at room temperature for four hours. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and ethyl ether (20:80). After evaporation of the solvents, 2.6 g (79%) of the expected product, melting point 168°-169° C., are collected.

Workup

  1. extractionthe mixture is extracted with ethyl ether
  2. customthe organic phase is separated after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a silica column
  7. washeluted with a mixture of dichloromethane and ethyl ether (20:80)
  8. customAfter evaporation of the solvents, 2.6 g (79%) of the expected product, melting point 168°-169° C.
  9. customare collected

Sources & evidence

ORD record
ord-65ff4a7df1f542cdae2ecd90533a09db
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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