Hydrochloric Acid → HCID 54407823, compound

HRID 343869Notes

Reaction equation

HRID 343869 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]([F:17])=[C:8]2[C:3]=1[C:4](=[O:18])[CH2:5][CH2:6][S:7]2.[Cl-].[Na+].[BH4-].[Na+].Cl>ClCCl.CO>[OH:18][CH:4]1[C:3]2[C:8](=[C:9]([F:17])[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]=2[Cl:1])[S:7][CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 54010744HCID 54010744, compound

Product 1

HCID 54407823HCID 54407823, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

30 ml of methanol and 20 ml of dichloromethane were added to 7.4 g (25.6 mmol) of 5-chloro-6-ethoxycarbonyl-8-fluorothiochroman-4-one (corresponding to compound of the formula (VIII)). While the mixture was maintained at a temperature not exceeding 0° C. with a sodium chloride aqueous solution and an ice bath, 0.97 g (25.6 mmol) of sodium borohydride as a reducing agent was gradually added. The mixture was allowed to react at room temperature for 3 hours, and then the reaction mixture was poured into a 5% hydrochloric acid aqueous solution and extracted with dichloromethane. The resultant organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel; hexane:ethyl acetate=2:1) to give 2.9 g (yield 40%) of 4-hydroxy-5-chloro-6-ethoxycarbonyl-8-flurothiochroman (corresponding to compound of the formula (IX)).

Workup

  1. temperatureWhile the mixture was maintained at a temperature not
  2. additionwas gradually added
  3. customto react at room temperature for 3 hours
  4. extractionextracted with dichloromethane
  5. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by column chromatography (silica gel; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5f49fb74c2b94dfeae19a3fefc682099
Source dataset
uspto-grants-1999_01
Patent number
US05863866

Reaction notes

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