Sodium Hydroxide → HCID 66762854, compound

HRID 573777Notes

Reaction equation

HRID 573777 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>ClCCl.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:19])([CH2:14][OH:15])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 66762362HCID 66762362, compound

Product 1

HCID 66762854HCID 66762854, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

3.1 g Diethyl 2-(4-iodophenyl)-2-methylmalonate are dissolved in 50 ml dichloromethane and cooled to −78° C. 50 ml of a 1 M solution of diisobutylaluminium hydride in dichloromethane are added dropwise and the mixture is warmed to −10° C. during 5 hours. Then 0.9 ml water and 0.9 ml of a 4 M solution of sodium hydroxide in water are added successively under cooling. The mixture is stirred vigorously for 10 minutes and is then partitioned between 600 ml ethylacetate and 500 ml of a 0.5 M hydrochloric acid. The organic phase is washed with brine and dried with magnesium sulphate. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (petrole ether/ethylacetate 40:60 to 0:100).

Workup

  1. temperaturethe mixture is warmed to −10° C. during 5 hours
  2. temperatureunder cooling
  3. customis then partitioned between 600 ml ethylacetate and 500 ml of a 0.5 M hydrochloric acid
  4. washThe organic phase is washed with brine
  5. dry with materialdried with magnesium sulphate
  6. customThe solvents are evaporated in vacuo
  7. customthe residue is chromatographed on silica gel (petrole ether/ethylacetate 40:60 to 0:100)

Sources & evidence

ORD record
ord-59a4e74d38b0452bac1f3b1298d61b34
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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