Ammonium Chloride → HCID 69944199, compound

HRID 1937151Notes

Reaction equation

HRID 1937151 reaction equation
Cl[CH2:2][Si:3]([CH3:9])([CH3:8])[O:4][CH:5]([CH3:7])[CH3:6].[Mg:10].[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[C:19](=[O:29])[C@H:20]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH3:21].[Cl-:30].[NH4+]>O1CCCC1>[CH3:8][Si:3]([CH2:2][Mg:10][Cl:30])([CH3:9])[O:4][CH:5]([CH3:7])[CH3:6].[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[C@:19]([OH:29])([C@H:20]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH3:21])[CH2:2][Si:3]([O:4][CH:5]([CH3:7])[CH3:6])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 266137(Chloromethyl)dimethylisopropoxysilaneHCID 5462224MagnesiumHCID 69943808HCID 69943808, compound

Product 2

HCID 69944199HCID 69944199, compoundHCID 178460657HCID 178460657, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(Dimethylisopropoxysilyl)methylmagnesium chloride was prepared from a solution of 5.74 g (34.4 mmol) of chloromethyldimethylisopropoxysilane in 40 ml tetrahydrofuran and 0.84 g (34.4 mmol) of metallic magnesium. A solution of 4.65 g (17.2 mmol) of (2R)-2′,3′-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone [prepared as described in Step 7(i) above] in 20 ml of tetrahydrofuran was added to the solution of the Grignard reagent at 0° C. with stirring. The resulting mixture was stirred at ambient temperature for 30 minutes, after which the reaction was stopped by the addition of a saturated aqueous ammonium chloride solution to the reaction mixture. The reaction product was extracted with ethyl acetate. The organic layer was washed with aqueous sodium chloride solution and concentrated to afford 8.1 g of crude (2S,3R)-2-(2,3-difluorophenyl)-1-(isopropoxydimethylsilyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-2-butanol as an oil.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 30 minutes
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium chloride solution
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5fa380011da44907994c362274a60505
Source dataset
uspto-grants-2002_05
Patent number
US06392082B1

Reaction notes

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