Ammonium Chloride → HCID 54141745, compound

HRID 1637516Notes

Reaction equation

HRID 1637516 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([O:18][CH3:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:20]([Mg]Br)[CH2:21][CH2:22][CH2:23][CH3:24].[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]([OH:15])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:12]([O:18][CH3:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19348493HCID 19348493, compoundHCID 178445865HCID 178445865, compound

Product 1

HCID 54141745HCID 54141745, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 27.91 g (99.5 mmol) of 4-t-butyldimethylsilyloxymethyl-2-methoxybenzaldehyde (prepared as described in Preparation 40) in 100 ml of tetrahydrofuran was added dropwise to 100 ml of an ice-cooled 1.62 M solution of pentylmagnesium bromide in tetrahydrofuran over a period of 30 minutes, and then the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was then mixed with a saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with a mixture of ethyl acetate and hexane. The extract was washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 250 g of silica gel using a 1:5 by volume mixture of ethyl acetate and hexane as the eluent, to give 30.67 g (yield 87%) of the title compound as an oily substance.

Workup

  1. extractionthe resulting mixture was extracted with a mixture of ethyl acetate and hexane
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialafter which it was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through 250 g of silica gel using a 1:5
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-e5961e5953cc4e0f9c1fcaaf8122c441
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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