Ammonium Chloride → HCID 67591974, compound

HRID 1419633Notes

Reaction equation

HRID 1419633 reaction equation
C([O:4][C@H:5]1[CH2:10][C@H:9]([O:11]C(=O)C)[CH2:8][CH:7]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]1[CH3:33])(=O)C.C[Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH3:30][C:29]([Si:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:15][CH:7]1[CH2:8][C@@H:9]([OH:11])[CH2:10][C@H:5]([OH:4])[CH:6]1[CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67592151HCID 67592151, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67591974HCID 67591974, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

469 mg (1 mmol) of 16 is dissolved in 10 ml of THF and mixed at 0° C. with 3.4 ml of methylmagnesium bromide solution (3M in THF). After 3 hours at this temperature, it is hydrolyzed with ammonium chloride solution, extracted with ethyl acetate and dried on sodium sulfate. The solvent is removed, and the residue is purified on silica gel (mobile solvent: EE:H=8.2), whereby 231 mg (0.6 mmol) of title compound 17 is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried on sodium sulfate
  3. customThe solvent is removed
  4. customthe residue is purified on silica gel (mobile solvent: EE:H=8.2)

Sources & evidence

ORD record
ord-709a02e3cb0f4d95b00e82e9f5bbc22d
Source dataset
uspto-grants-1999_03
Patent number
US05886233

Reaction notes

Loading…