Water → HCID 69837663, compound

HRID 2083915Notes

Reaction equation

HRID 2083915 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:13]([F:15])[F:14])[CH:11]=1)S[CH2:7][CH2:6][C@@:5]2([C:17]([OH:19])=[O:18])[OH:16].O.O[O:22][S:23]([O-:25])=O.[K+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:13]([F:14])[F:15])[CH:11]=1)[S:23](=[O:25])(=[O:22])[CH2:7][CH2:6][C@@:5]2([C:17]([OH:19])=[O:18])[OH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 69838792HCID 69838792, compound

Product 1

HCID 69837663HCID 69837663, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of (R)-6-chloro-8-difluoromethoxy-4-hydroxythiochromane-4-yl-carboxylic acid (0.50 g, 1.6 mmol; from step (vi) above), wet alumina (prepared by adding H2O (1 mL) to alumina (5.0 g) and shaking until a free flowing powder was obtained, ca. 0.82 g, 8.0 mmol), and Oxone® (4.9 g, 8.0 mmol) in CHCl3 (19 mL) was heated to 40-45° C. for 20 h. The reaction was cooled to room temperature, filtered through a Buichner funnel with EtOAc (50 mL), and concentrated in vacuo to afford 0.54 g (98%) of the sub-title compound as a brown foam which was used without further purification.

Workup

  1. customprepared
  2. customwas obtained
  3. filtrationfiltered through a Buichner funnel with EtOAc (50 mL)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c1b164428ab46b0851ab1a56b4493d8
Source dataset
uspto-grants-2004_04
Patent number
US06716834B2

Reaction notes

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