Ethyl acetate hexane → HCID 66648815, compound

HRID 1774409Notes

Reaction equation

HRID 1774409 reaction equation
[Si:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][C:14]2[C:15]([O:17][C:18](=O)C=2C(C)C)=[O:16])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si](C=[N+]=[N-])(C)C.[CH3:33][CH2:34][CH2:35]CCC.CCCCCC.[C:45]([O:48][CH2:49]C)(=[O:47])[CH3:46]>CO>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13]/[C:14](=[C:46](\[CH:34]([CH3:35])[CH3:33])/[C:45]([O:48][CH3:49])=[O:47])/[C:15]([O:17][CH3:18])=[O:16])=[CH:24][CH:25]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 59706497HCID 59706497, compoundHCID 86587183Trimethylsilyldiazomethane hexane

Product 1

HCID 66648815HCID 66648815, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(t-butyldimethylsilyloxy)benzyl]-3-isopropylmaleic anhydride (823 mg, 2.28 mmol) in methanol (15 mL) was added a 2.0 M trimethylsilyl diazomethane-hexane solution (8.5 mL, 17 mmol) with stirring at room temperature. After stirring at room temperature for 30 min, the reaction mixture was concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 10:1→8:1) to give 913 mg of dimethyl 2-[4-(t-butyldimethylsilyloxy)benzyl]-3-isopropylmaleate as oil (yield: 98%).

Workup

  1. stirringAfter stirring at room temperature for 30 min
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-64111429f7184c26bd3b0dce3645aeae
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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