Sodium Bicarbonate → HCID 68152517, compound

HRID 931851Notes

Reaction equation

HRID 931851 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]1(O)[CH2:12][CH2:11][CH2:10]1.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]1[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 70559507HCID 70559507, compound

Product 1

HCID 68152517HCID 68152517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14.5 g (47.39 mmol) of 4 are dissolved in 50 ml of THF under nitrogen, and 35.72 ml (284.4 mmol) of boron trifluoride/diethyl ether complex are added dropwise at room temperature, and 12.54 g (189.6 mmol) of sodium cyanoborohydride are added dropwise in portions. The batch is heated under reflux overnight. The batch is allowed to cool to room temperature, sat. NaHCO3 solution is added, the mixture is extracted with methyl t-butyl ether, the organic phase is dried over sodium sulfate and filtered, the solvent is removed in vacuo, and the residue is filtered through silica gel with 1-chlorobutane, giving 5 as a yellow liquid.

Workup

  1. addition35.72 ml (284.4 mmol) of boron trifluoride/diethyl ether complex are added dropwise at room temperature
  2. temperatureThe batch is heated
  3. temperatureunder reflux overnight
  4. extractionthe mixture is extracted with methyl t-butyl ether
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo
  8. filtrationthe residue is filtered through silica gel with 1-chlorobutane

Sources & evidence

ORD record
ord-15957b0c6e4840efaa9deb74301ff729
Source dataset
uspto-grants-2016_03
Patent number
US09296948B2

Reaction notes

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