Dichloromethane → HCID 59779129, compound

HRID 1096753Notes

Reaction equation

HRID 1096753 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]23[CH2:14][CH:13]2[CH2:12][O:11][C:10]3=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8].ClCCl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH2:10][OH:15])[CH2:14][CH:13]2[CH2:12][OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 59779141HCID 59779141, compound

Product 1

HCID 59779129HCID 59779129, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS (10.9 mL, 115 mmol) was added to (1S)-1-(3,4-dichloro-phenyl)-3-oxabicyclo[3.1.0]hexan-2-one (14 g, 57.6 mmol) in dry tetrahydrofuran (140 mL), under nitrogen atmosphere. The reaction mass was refluxed for 5 hours and monitored by TLC (dichloromethane (100%)). The reaction was quenched with 10% potassium carbonate solution. The aqueous layer was extracted with dichloromethane (2×250 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to yield 14 g (98.5%) of desired product. 1H NMR δ(300 MHz,CDCl3): 0.9-0.98 (1H,m), 1.17 (1H,m), 1.48 (1H,m), 3.23-3.42 (2H,m) 3.92-4.03 (2H,m) 7.10-7.13 (1H,m), 7.24-7.27 (1H,m), 7.38 (1H,m,).

Workup

  1. temperatureThe reaction mass was refluxed for 5 hours
  2. customThe reaction was quenched with 10% potassium carbonate solution
  3. extractionThe aqueous layer was extracted with dichloromethane (2×250 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2b3cf1fd86fc42fea305a0ade98886bd
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

Loading…