HCID 86750890, compound → HCID 86750889, compound

HRID 1781541Notes

Reaction equation

HRID 1781541 reaction equation
[CH3:1][S:2]([O:5][C:6]1[C:14]([CH2:15]/[CH:16]=[C:17](/[Cl:25])\[C:18]([O:20]C(C)(C)C)=[O:19])=[C:13]([O:26][CH3:27])[C:12]([CH3:28])=[C:11]2[C:7]=1[C:8](=[O:29])[O:9][CH2:10]2)(=[O:4])=[O:3]>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:1][S:2]([O:5][C:6]1[C:14]([CH2:15]/[CH:16]=[C:17](/[Cl:25])\[C:18]([OH:20])=[O:19])=[C:13]([O:26][CH3:27])[C:12]([CH3:28])=[C:11]2[C:7]=1[C:8](=[O:29])[O:9][CH2:10]2)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 86750890HCID 86750890, compound

Product 1

HCID 86750889HCID 86750889, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

t-Butyl (E)-4-(1,3-dihydro-4-methanesulfonyloxy-6-methoxy-7-methyl -3-oxoisobenzofuran-5-yl)-2-chlorobut-2-enoate (2.7 g) was dissolved in freshly distilled trifluoroacetic acid (25 ml) and stirred at room temperature for 90 minutes. The mixture was diluted with CH2Cl2 (25 ml) and evaporated to dryness and repeated until a cream solid was obtained. The solid was recrystallized from a 4:1 mixture of hexanes-CH2CH2 (25 ml) affording 2.11 g of (E)-4-(1,3-dihydro-4-methanesulfonyloxy-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-2-chlorobut-2-enoic acid as white crystals, mp 200°-203° (d).

Workup

  1. customevaporated to dryness
  2. customwas obtained
  3. customThe solid was recrystallized from a 4:1 mixture of hexanes-CH2CH2 (25 ml)

Sources & evidence

ORD record
ord-d3b13ccbffa14eb7a6ef6bc77b1e81ca
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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