Sodium Bicarbonate → 6-(But-3-ynyloxy)hexanal

HRID 2118177Notes

Reaction equation

HRID 2118177 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[CH:12].C(=O)(O)[O-:14].[Na+]>CS(C)=O.C(OCC)C>[CH2:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[O:14])[CH2:10][C:11]#[CH:12]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 113792816-Bromohexylbut-3-ynyl ether

Product 1

HCID 218670216-(But-3-ynyloxy)hexanalYield 85.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

6-Bromohexylbut-3-ynyl ether (DE3513885A1) (525 mg) in DMSO (2 ml) was added to a mixture of sodium bicarbonate (1 g) in DMSO (8 ml) at 150° C. with vigorous stirring and nitrogen bubbling through the solution. The mixture was stirred for 20 min at 150° C. and then allowed to cool to room temperature, diluted with diethyl ether and washed with water. The aqueous layer was extracted with diethyl ether and the combined ether layers were washed with dilute hydrochloric acid, brine, dried (MgSO4) and evaporated to dryness to give the title compound (325 mg): IR 1726 cm−1 MS(TSP+ve) m/z 186 (M+MH4)+.

Workup

  1. stirringThe mixture was stirred for 20 min at 150° C.
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. washthe combined ether layers were washed with dilute hydrochloric acid, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-453268aa798341ee9168919cc868cc3e
Source dataset
uspto-grants-2008_10
Patent number
US07442836B2

Reaction notes

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