Hydrochloric Acid → HCID 178499702, compound

HRID 1005341Notes

Reaction equation

HRID 1005341 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]([C@@H:11]1[CH2:14][C@H:13]([CH:15]([C:26]([O:28][CH3:29])=[O:27])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)=[O:10].Br[CH2:31][C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH3:29][O:28][C:26]([C:15]([C@H:13]1[CH2:14][C@@H:11]([C:9]([O:8][CH3:7])=[O:10])[CH2:12]1)([CH2:31][C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1)[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1378441-(Bromomethyl)naphthaleneHCID 23665647Potassium tert-butoxideHCID 178500963HCID 178500963, compound

Product 1

HCID 178499702HCID 178499702, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of potassium t-butoxide (0.44 g, 3.93 mmol) in dry tetrahydrofuran (20 ml) cooled to 0° C. under a nitrogen atmosphere was added dropwise a solution of benzyl methyl cis-3-methoxycarbonylcyclobutylmalonate (1.25 g, 3.9 mmol) in dry tetrahydrofuran (20 ml) followed by dropwise addition of 1-(bromomethyl)naphthalene (2.58 g, 11.7 mmol) in dry toluene (15 ml). Stirring was continued at 0° C. for 4 hours, aqueous hydrochloric acid (2M, 15 ml) was then added and the mixture extracted with diethyl ether. The organic phase was dried, filtered and evaporated to an oil (2.5 g). The oil was dissolved in dichloromethane and filtered through a pad of flash silica, the solvent was removed and the resulting oil (2.0 g) purified by chromatography on silica using a Biotage Flash 40 eluting with dichloromethane to give the title compound as a colourless oil.

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated to an oil (2.5 g)
  5. dissolutionThe oil was dissolved in dichloromethane
  6. filtrationfiltered through a pad of flash silica
  7. customthe solvent was removed
  8. customthe resulting oil (2.0 g) purified by chromatography on silica using a Biotage Flash 40 eluting with dichloromethane

Sources & evidence

ORD record
ord-5834445cc0704b3f841e059e0f92b299
Source dataset
uspto-grants-2000_04
Patent number
US06054448

Reaction notes

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