(Dimethyl sulfide)trihydroboron → HCID 178462225, compound

HRID 962995Notes

Reaction equation

HRID 962995 reaction equation
B.CSC.[C:5]([C-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)(=[O:7])[CH3:6].[C-:13]1([C:18](=[O:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:21]>O1CCCC1>[OH:7][C@@H:5]([C-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)[CH3:6].[C-:13]1([C@H:18]([OH:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:21]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 178466059HCID 178466059, compound

Product 1

HCID 178462225HCID 178462225, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.5 ml (115 mmol) of borane-dimethyl sulphide adduct were added dropwise at 20° C. to a solution of 30.0 g (111 mmol) of 1,1'-diacetylferrocene and 13.5 ml (13.5 mmol, 0.12 eq) of catalyst (S)-III (R6 =CH3) in 200 ml of tetrahydrofuran over a period of 45 minutes. After 1 hour at 20°-25° C., the reaction mixture was poured while stirring vigorously onto about 600 ml of ice/water and stirred for 0.5 hour. 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 32.7 g (107%) of the crude title compound. This crude product can be used without further purification for the further reactions. Recrystallization from hexane gave (R,R)-1,1'-bis(1-hydroxyethyl)ferrocene as a yellow crystalline solid.

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
  6. customRecrystallization from hexane

Sources & evidence

ORD record
ord-621deaa44a274eafb1a86828f5d305ae
Source dataset
uspto-grants-1998_06
Patent number
US05760264

Reaction notes

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