Water → HCID 178462227, compound

HRID 962990Notes

Reaction equation

HRID 962990 reaction equation
O1CCCC1.[C:6]([C-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)(=[O:8])[CH3:7].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19].B.CSC.O>COC(C)(C)C>[OH:8][C@@H:6]([C-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[CH3:7].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 12423031(Dimethyl sulfide)trihydroboronHCID 178466060HCID 178466060, compound

Product 1

HCID 178462227HCID 178462227, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Subsequently, 1.0 l of tetrahydrofuran and 750 g (3.29 mol) of acetylferrocene (dried overnight at 40° C. in vacuo) were added to the catalyst solution thus obtained and dissolved by further addition of 1.0 l of tetrahydrofuran. The amount of catalyst was thus 6.8 mol%. At 20°-25° C., a further 145 ml of borane-dimethyl sulphide adduct (1.75 mol altogether) was added dropwise and uniformly over a period of 3 hours. After stirring for a further 30 minutes, the reaction mixture was hydrolysed while cooling by addition of 2.0 l of water, with care being taken to ensure that the temperature did not rise above 30° C. Subsequently, 2.0 l of tert-butyl methyl ether were added, the phases were separated and the aqueous phase was extracted once more with 1.0 l of tert-butyl methyl ether. The combined organic phases were dried over magnesium sulphate and the solvent was distilled off.

Workup

  1. customthus obtained
  2. customdid not rise above 30° C
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted once more with 1.0 l of tert-butyl methyl ether
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d26c62c167264eb4bfb63464ebf5d63b
Source dataset
uspto-grants-1998_06
Patent number
US05760264

Reaction notes

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