Sulfuric Acid → HCID 67125523, compound

HRID 920606Notes

Reaction equation

HRID 920606 reaction equation
[F:1][CH:2]([F:22])[O:3][C:4]1[C:9]2[O:10][C:11]3([O:17][C:8]=2[C:7]([C:18]([O:20]C)=[O:19])=[CH:6][CH:5]=1)[CH2:16][CH2:15][S:14][CH2:13][CH2:12]3.S(=O)(=O)(O)O>CO.C1COCC1.[OH-].[Li+]>[F:22][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3([O:17][C:8]=2[C:7]([C:18]([OH:20])=[O:19])=[CH:6][CH:5]=1)[CH2:16][CH2:15][S:14][CH2:13][CH2:12]3

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 67125492HCID 67125492, compound

Product 1

HCID 67125523HCID 67125523, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-Difluoromethoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylate (437 mg) was dissolved in a mixture of Methanol (5 mL) and THF (5 mL) and 1M aqueous Lithium hydroxide (3.9 mL) was added. The ester was cleaved after 1 hour at 50° C. The solution was cooled to room temperature and acidified with 2N sulfuric acid (1.95 mL) and the product was extracted into EtOAc. 7-Difluoromethoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylic acid was obtained after removal of solvents under reduced pressure.

Workup

  1. additionwas added
  2. extractionthe product was extracted into EtOAc

Sources & evidence

ORD record
ord-0560e71dfe5346d3a116cb50c2827d6e
Source dataset
uspto-grants-2016_03
Patent number
US09273064B2

Reaction notes

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