Ammonium Chloride → HCID 69944199, compound

HRID 1250375Notes

Reaction equation

HRID 1250375 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-e648efe6eabd4489960bb10fc1ea0cb7
Source dataset
uspto-grants-2002_01
Patent number
US06337403B1

Reaction notes

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