Borane;tetrahydrofuran → HCID 58256115, compound

HRID 1365620Notes

Reaction equation

HRID 1365620 reaction equation
[C:1]([CH2:4][C:5]1[C:9]([Cl:10])=[C:8]([Cl:11])[S:7][C:6]=1[CH2:12][C:13](O)=[O:14])(O)=[O:2].B.C1COCC1>C1COCC1>[Cl:10][C:9]1[C:5]([CH2:4][CH2:1][OH:2])=[C:6]([CH2:12][CH2:13][OH:14])[S:7][C:8]=1[Cl:11]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 66934474HCID 66934474, compound

Product 1

HCID 58256115HCID 58256115, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

A solution of the product from step (d) (2.5 g, 9.33 mmol) in THF (85 ml) was cooled to 0° C. and a 1M solution of BH3-THF (46.6 ml, 46.6 mmol) was added dropwise over 10 min. and stirred for an additional 20 minutes after the addition was complete. The reaction was warmed to 22° C. and stirred for 2 hours. The reaction was poured into-ice cold sat. NaHCO3 (150 ml) and extracted with EtOAc. The crude was passed through a plug of silica gel washing with EtOAc. Concentration of the eluent provided 1.99 g (88%) of the subtitle compound.

Workup

  1. additionafter the addition
  2. stirringstirred for 2 hours
  3. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-77e883ea8724498fa5b1f2a640a9b259
Source dataset
uspto-grants-2011_02
Patent number
US07893051B2

Reaction notes

Loading…