(Dimethyl sulfide)trihydroboron → HCID 178456098, compound

HRID 962993Notes

Reaction equation

HRID 962993 reaction equation
B.CSC.[C:5]([C-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)(=[O:8])[CH2:6][CH3:7].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19]>O1CCCC1>[OH:8][C@@H:5]([C-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[CH2:6][CH3:7].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 178458220HCID 178458220, compound

Product 1

HCID 178456098HCID 178456098, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 ml (25 mmol) of borane-dimethyl sulphide adduct were added dropwise at 200C to a solution of 10.0 g (41.3 mmol) of propionylferrocene and 2.5 ml (2.5 mmol, 0.06 eq) of catalyst (S)-III (R6 =CH3) in 30 ml of tetrahydrofuran over a period of 30 minutes. After 1 hour at 20°-25° C., the reaction mixture was poured while stirring vigorously onto about 200 ml of ice/water and stirred for 0.5 hours. The aqueous phase was subsequently extracted three times with 200 ml each time of tert-butyl methyl ether, the combined organic phases were dried over magnesium sulphate and evaporated in a high vacuum. This gave 10.7 g (106%) of the crude title compound. This crude product can be used without further purification for the further reactions.

Workup

  1. additionthe reaction mixture was poured
  2. extractionThe aqueous phase was subsequently extracted three times with 200 ml each time of tert-butyl methyl ether
  3. dry with materialthe combined organic phases were dried over magnesium sulphate
  4. customevaporated in a high vacuum
  5. customThis crude product can be used without further purification for the further reactions

Sources & evidence

ORD record
ord-bd9432f489824912813f007581ff038a
Source dataset
uspto-grants-1998_06
Patent number
US05760264

Reaction notes

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