Dichloromethane → HCID 59779170, compound

HRID 1096755Notes

Reaction equation

HRID 1096755 reaction equation
[C:1]1([C@:11]23[CH2:16][CH:15]2[CH2:14][O:13][C:12]3=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClCCl>O1CCCC1>[C:1]1([C@:11]2([CH2:12][OH:17])[CH2:16][CH:15]2[CH2:14][OH:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 59779125HCID 59779125, compound

Product 1

HCID 59779170HCID 59779170, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS (0.2 mL, 0.8 mmol) was added to (1S)-1-(1-naphthyl)-3-oxabicyclo[3.1.0]hexan-2-one (90 mg, 0.4 mmol) in dry tetrahydrofuran (1 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 (2×10 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to yield 90 mg (98.5%) of desired product. 1H NMR δ(300 MHz,CDCl3): 1.09-1.43 (3H,m), 1.67-1.69 (2H,m,) 1.83-1.90 (1H,m), 3.5-3.7 (2H,m), 4.25-4.27 (2H,m), 7.4-7.65 (4H,m), (1H,m) 7.77-7.89 (2H,m), 8.25 (1H,brs).

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 (2×10 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-6df09ca241e54a0c838c8ba166d19c0b
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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