Sodium hydride → HCID 14621498, compound

HRID 1651672Notes

Reaction equation

HRID 1651672 reaction equation
[OH:1]/[N:2]=[CH:3]/[C@H:4]1[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:8][O:7][C@@H:6]([CH3:20])[O:5]1.[H-].[Na+].[C:23]1([CH:29](Br)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O.C(OCC)(=O)C>[C:23]1([CH:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:1]/[N:2]=[CH:3]/[C@H:4]2[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:8][O:7][C@@H:6]([CH3:20])[O:5]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 236603BromodiphenylmethaneHCID 14621496HCID 14621496, compound

Product 1

HCID 14621498HCID 14621498, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,4R,5S)-(E)-4-hydroxyiminomethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (100 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (14 mg 60% in oil) at 5° C. After being stirred at the same temperature for 30 minutes, to the solution was added diphenylmethyl bromide (86.6 mg) and the mixture was stirred in an ice bath for additional 2 hours. The solution was diluted with ethyl acetate and washed successively with water and brine, dried over magnesium sulfate. The solvent was evaporated in vacuo and the crude residue was purified with preparative TLC with a mixture of n-hexane and ethyl acetate (4:1) as an eluent to give (2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

Workup

  1. stirringthe mixture was stirred in an ice bath for additional 2 hours
  2. washwashed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe crude residue was purified with preparative TLC with a mixture of n-hexane and ethyl acetate (4:1) as an eluent

Sources & evidence

ORD record
ord-ef8cd9fce3ab44139d22054ac9bd2025
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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