(Dimethyl sulfide)trihydroboron → HCID 57518698, compound

HRID 1258127Notes

Reaction equation

HRID 1258127 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][CH2:8][C@:7]([CH2:11][CH2:12][C:13](O)=[O:14])([CH3:10])[C:6]1([CH3:17])[CH3:16])=[O:4].CSC.B>C1COCC1>[OH:14][CH2:13][CH2:12][CH2:11][C@:7]1([CH3:10])[CH2:8][CH2:9][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]1([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 57518697HCID 57518697, compound

Product 1

HCID 57518698HCID 57518698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of step 5 intermediate (0.645 g, 2.66 mmol) in dry THF (10 mL) under N2 atmosphere, borane dimethylsulphide (0.328 mL, 3.46 mmol) was added slowly for 30 min through a septum and stirred for overnight. The reaction mixture was quenched with water, oxone then stirred for 30 mins. Then the reaction mixture was extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure to afford the desired product (0.565 g) as colorless liquid. m/z (M+18): 246.

Workup

  1. customThe reaction mixture was quenched with water, oxone
  2. stirringthen stirred for 30 mins
  3. extractionThen the reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0276c02443d14e408d56d52e058802f7
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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