Lithium Chloride → HCID 86700877, compound

HRID 881773Notes

Reaction equation

HRID 881773 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[O:14][C:11]([CH2:15][CH:16](C(OC)=O)[C:17]([O:19][CH3:20])=[O:18])([CH2:12][CH2:13]2)[CH2:10][CH2:9]3)=[CH:4][CH:3]=1.[Cl-].[Li+]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[O:14][C:11]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])([CH2:10][CH2:9]2)[CH2:12][CH2:13]3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 86700878HCID 86700878, compound

Product 1

HCID 86700877HCID 86700877, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
180 °C

Procedure

To a solution of dimethyl 2-((4-(4-bromophenyl)-7-oxabicyclo[2.2.1]heptan-1-yl)methyl)malonate (305 mg, 0.77 mmol) in DMSO (3.0 mL) and water (0.03 mL) was added lithium chloride (98 mg, 2.3 mmol) and the reaction was stirred in a microwave reactor at 180° C. for 20 min. The resulting yellow reaction mixture was diluted with water and extracted with EtOAc. The organic phase was dried over MgSO4, filtered and concentrated by rotary evaporation in vacuo to afford 289 mg of a crude clear yellow film. Purification of the crude material by column chromatography (24 g silica gel, 0-30% EtOAc:Hept, monitor 230 nm) afforded 194 mg colorless film that solidified upon standing and which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.54-1.67 (m, 4H), 1.68-1.79 (m, 2H), 2.04-2.16 (m, 4H), 2.42-2.48 (m, 2H), 3.61 (s, 3H), 7.31 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.6 Hz, 2H). ESI-MS m/z: 341.1 [M+H]+, retention time 1.59 min (condition E).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation in vacuo
  5. customto afford 289 mg of a crude clear yellow film
  6. customPurification of the crude material by column chromatography (24 g silica gel, 0-30% EtOAc:Hept, monitor 230 nm)
  7. customafforded 194 mg colorless film that
  8. customwhich was used without further purification

Sources & evidence

ORD record
ord-42c8c6ca30a6498ba89af3881cc2cd0f
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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