Sodium borohydride → HCID 9818164, compound

HRID 1736492Notes

Reaction equation

HRID 1736492 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C.O.O.O.O.O.O.[Co](Cl)Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19433114HCID 19433114, compound

Product 1

HCID 9818164HCID 9818164, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of 3-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydrothiophene 1,1-dioxide (1.2 g; which is prepared as described in Example 13) in ethanol (50 mL) is treated with sodium borohydride (0.45 g) followed by cobalt dichloride hexahydrate (0.94 g), and the purple mixture is stirred at room temperature for 6 hours. It is then filtered through a pad of diatomaceous earth, and the pad is washed with dichloromethane (150 mL). The combined flitrate and washings are evaporated, and the resulting residue is subjected to flash chromatography on silica gel, using a mixture of ethyl acetate and toluene as eluent, to give an oil which slowly crystallizes. It is recrystallized from ethyl acetate at -40° C., to give 3-(3-cyclopentyloxy-4methoxyphenyl)tetrahydrothiophene 1,1-dioxide (0.74 g) in the form of a white solid, m.p. 89°-90° C. [Elemental analysis: C,61.8; H,7.10; S,10.4%; calculated: C,61.91; H,7.1; S,10.33%].

Workup

  1. filtrationIt is then filtered through a pad of diatomaceous earth
  2. washthe pad is washed with dichloromethane (150 mL)
  3. customThe combined flitrate and washings are evaporated
  4. additiona mixture of ethyl acetate and toluene as eluent
  5. customto give an oil which
  6. customslowly crystallizes
  7. customIt is recrystallized from ethyl acetate at -40° C.

Sources & evidence

ORD record
ord-b835b252543d4cc798e8e1dc617afc10
Source dataset
uspto-grants-1996_07
Patent number
US05541219

Reaction notes

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