Dichloromethane → HCID 59779155, compound

HRID 1096752Notes

Reaction equation

HRID 1096752 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 59779171HCID 59779171, compound

Product 1

HCID 59779155HCID 59779155, compoundYield 917.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS (17.16 mL, 18 mmol) was added to (1R)-1-(3,4-dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one (22 g, 9 mmol) in dry tetrahydrofuran (200 mL), under nitrogen atmosphere. The reaction mass was refluxed for 5 hours and monitored by TLC (dichloromethane (100%)). The reaction mass 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 sulfate, filtered and evaporated under reduced pressure to yield 20.4 g (92%) of desired product. 1H NMR δ(300 MHz,CDCl3): 0.9-1.25 (1H,m), 1.35-1.52 (1H,m), 1.75-1.79 (1H,m), 3.32-3.42 (2H,m) 3.97-4.12 (2H,m) 7.26-7.30 (1H,dd,J=8.4,2.1 Hz), 7.40-7.43 (1H,d,J=8.4 Hz), 7.52-7.53 (1H,d,J=2 Hz).

Workup

  1. temperatureThe reaction mass was refluxed for 5 hours
  2. customThe reaction mass 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 sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e65856d33c254655a54c745acbc3619d
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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