Ethyl acetate hexane → HCID 178439350, compound

HRID 1774392Notes

Reaction equation

HRID 1774392 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH:15]([C:24](O)=[O:25])[C:16](O)([CH:20]([CH3:22])[CH3:21])[C:17]([OH:19])=[O:18])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCCCCC.C(OCC)(=O)C>C(OC(=O)C)(=O)C>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[C:24]([O:18][C:17](=[O:19])[C:16]=2[CH:20]([CH3:21])[CH3:22])=[O:25])[CH2:11][CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 178454386HCID 178454386, compound

Product 1

HCID 178439350HCID 178439350, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

3-(Trans-4-t-butyldimethylsilyloxycyclohexyl)-2-hydroxy-2-isopropylsuccinic acid (510 mg, 1.31 mmol) was dissolved in acetic anhydride (5.5 mL), and the solution was stirred at 120° C. for 18 h. The acetic anhydride was evaporated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 50:1) to give 293 mg of 2-(trans-4-t-butyldimethylsilyloxycyclohexyl)-3-isopropylmaleic anhydride as oil (yield: 63%).

Workup

  1. customThe acetic anhydride was evaporated under reduced pressure
  2. customthe residue thus obtained

Sources & evidence

ORD record
ord-e3401273d9e246aba333f048fc631178
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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