Dichloromethane → HCID 59779150, compound

HRID 1096754Notes

Reaction equation

HRID 1096754 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 59779134HCID 59779134, compound

Product 1

HCID 59779150HCID 59779150, compoundYield 167%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS (8.10 mL, 107 mmol) was added to (1R)-1-(1-naphthyl)-3-oxabicyclo[3.1.0]hexan-2-one (12 g, 53.5 mmol) in dry tetrahydrofuran (100 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 (2×150 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): 0.87 (1H,m), 1.01-1.25 (2H,m,), 1.78-1.83 (2H,m,) 3.4-3.7 (2H,m), 4.12-4.18 (2H,m), 7.36-7.52 (4H,m), 7.57-7.75 (1H,m) 7.83-7.86 (1H,m) 8.25 (1H,brs).

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 (2×150 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-1ee104beb08b474cb18277aa0d3e257e
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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