Dimethylformamide → HCID 15735675, compound

HRID 1885549Notes

Reaction equation

HRID 1885549 reaction equation
[CH2:1]=[CH:2][CH2:3][CH:4]([OH:20])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[CH3:27]N(C)C=O>>[CH2:27]([O:20][CH:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][CH:2]=[CH2:1])[C:23]1[CH:22]=[CH:21][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8058HexaneHCID 15735674HCID 15735674, compound

Product 1

HCID 15735675HCID 15735675, compoundYield 72%

Procedure

To a solution of 11.0 g of 1-nonadecen-4-ol in 60 ml of dimethylformamide was added hexane-washed sodium hydride (from 2.34 g of a 50% oil dispersion). The reaction mixture was heated to 50° and 4.6 ml of benzyl bromide was added. The mixture was cooled to room temperature, quenched by the addition of water, and concentrated. The concentrate was diluted with water and then extracted with diethyl ether. The combined extracts were washed with water, dried over anhydrous sodium sulfate and concentrated to an oil. Purification of the oil by high pressure liquid chromatography utilizing diethyl ether/hexane (1:99) yielded 10.5 g (72%) of 4-benzyloxy-1-nonadecene as a liquid.

Workup

  1. washwashed sodium hydride (from 2.34 g of a 50% oil dispersion)
  2. temperatureThe reaction mixture was heated to 50°
  3. addition4.6 ml of benzyl bromide was added
  4. customquenched by the addition of water
  5. concentrationconcentrated
  6. additionThe concentrate was diluted with water
  7. extractionextracted with diethyl ether
  8. washThe combined extracts were washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated to an oil
  11. customPurification of the oil by high pressure liquid chromatography

Sources & evidence

ORD record
ord-b7a8aab473fd49b8b321f43958b43e48
Source dataset
uspto-grants-1992_09
Patent number
US05145844

Reaction notes

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