Ammonium Chloride → HCID 57049780, compound

HRID 1492006Notes

Reaction equation

HRID 1492006 reaction equation
[H-].[K+].[Si:3]([O:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C@@H:18]([OH:19])[CH2:17][O:16][C@@H:15]1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].I[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:30][CH:29]=1.[Cl-].[NH4+]>O1CCCC1>[C:31]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:30]=[CH:29][C:28]([CH2:27][O:19][C@H:18]2[CH2:17][O:16][C@H:15]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[C@@H:14]2[CH2:13][CH2:12][CH2:11][O:10][Si:3]([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 82127Potassium hydrideHCID 219099744-(Iodomethyl)biphenylHCID 57109009HCID 57109009, compound

Product 1

HCID 57049780HCID 57049780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

A 0.694 g (0.00346 mole) suspension of 20% potassium hydride in mineral oil is washed twice with petroleum ether and resuspended in 5 ml of tetrahydrofuran. The suspension is cooled with stirring at -15 ° C. and a solution of 1.169 g (0.00346 mole) of (2S,3S,4R)-3-(3-t-butyldimethylsilyloxyprop-1-yl)-4-hydroxy-2-(3-pyridyl)tetrahydrofurane in 10 ml of tetrahydrofurane is added dropwise. After stirring the mixture for 2 min, 1.37 g (0.00346 mole) of 4-iodomethylbiphenyl is added at once and the mixture is stirred at -15° C. for 75 min. Concentrated ammonium chloride is added and the mixture is extracted with ether (2×20 ml). The combined extracts are washed with water and brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography using ethyl acetate-methylene chloride (1:1) to give (2S,3S,4R)-4-(biphenyl-4-ylmethoxy)-3-(3-t-butyldimethylsilyloxyprop-1-yl)-2 -(3-pyridyl)tetrahydrofuran as an oil having [α]D25 =+71.99 MeOH).

Workup

  1. temperatureThe suspension is cooled
  2. stirringAfter stirring the mixture for 2 min
  3. stirringis stirred at -15° C. for 75 min
  4. extractionthe mixture is extracted with ether (2×20 ml)
  5. washThe combined extracts are washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-81aa8c5d317642e49713bca71e6f8b67
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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