Tetrahydrofuran → HCID 59497429, compound

HRID 1747465Notes

Reaction equation

HRID 1747465 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[O:12][C:11](=[O:14])[NH:10][C:9]=2[CH:8]=[C:7]([Cl:15])[CH:6]=1)=O.O1CCCC1.[Li+].[BH4-]>C(OCC)C>[Cl:15][C:7]1[CH:6]=[C:5]([CH2:3][OH:2])[C:13]2[O:12][C:11](=[O:14])[NH:10][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 59497315HCID 59497315, compound

Product 1

HCID 59497429HCID 59497429, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-Chloro-2-oxo-2,3-dihydro-benzooxazole-7-carboxylic acid methyl ester (8 g, 35 mmol) is suspended in diethyl ether (100 mL) and tetrahydrofuran (410 mL) and cooled to zero. The reaction is purged with nitrogen and LiBH4 (6.72 g, 310 mmol) is added portion wise to the reaction. The reaction is warmed to room temperature and stirred for 3 hours. Upon completion the reaction is cooled to 0° C. and quenched by the slow addition of saturated ammonium chloride (250 mL). Water is added to the reaction (500 mL) and the organic layer separated. The water layer is extracted with ethyl acetate (3×100 mL) and the combined organic layers are dried (Na2SO4) filtered and evaporated in vacuo. Product is purified on silica with dichloromethane methanol as the eluent to yield (4.2 g 31 mmol 60%) the title compound (4.2 g 31 mmol 60%). LCMS (ESMS): m/z 200.5 (M+H+).

Workup

  1. additionis added portion
  2. customwise to the reaction
  3. temperatureUpon completion the reaction is cooled to 0° C.
  4. customquenched by the slow addition of saturated ammonium chloride (250 mL)
  5. additionWater is added to the reaction (500 mL)
  6. customthe organic layer separated
  7. extractionThe water layer is extracted with ethyl acetate (3×100 mL)
  8. dry with materialthe combined organic layers are dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customProduct is purified on silica with dichloromethane methanol as the eluent

Sources & evidence

ORD record
ord-cdcce15cc3ca466fa074161dc5a51d91
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…