Acrolein → 1-Heptadecen-4-yn-3-ol

HRID 622106Notes

Reaction equation

HRID 622106 reaction equation
C([Mg]Br)C.[CH:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH:19]([CH:21]=[CH2:22])=[O:20].[Cl-].[NH4+]>C(OCC)C.O>[CH2:22]=[CH:21][CH:19]([OH:20])[C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 7847AcroleinHCID 25517Ammonium ChlorideHCID 698231-TetradecyneHCID 178418443HCID 178418443, compound

Product 1

HCID 142571091-Heptadecen-4-yn-3-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-10 °C

Procedure

To freshly prepared ethyl magnesium bromide (from 58.95 mmoles of bromoethane and 49.36 mmoles of magnesium) in diethyl ether (125 ml) was added 1-tetradecyne (44.5 mmoles) in diethyl ether (25 ml) dropwise at ambient temperature. After 3 hours the reaction mixture was cooled to -10° C. and freshly distilled acrolein (59.86 mmoles) in diethyl ether (25 ml) was added dropwise. After 30 minutes saturated ammonium chloride (100 ml) and water (50 ml) were added. The organic phase was separated, washed with brine (100 ml) and dried over anhydrous magnesium sulfate. The desired compound was purified by flash chromatography on silica gel eluted with 90:10 hexane:ethyl acetate.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe desired compound was purified by flash chromatography on silica gel
  5. washeluted with 90:10 hexane

Sources & evidence

ORD record
ord-d27980a078a84be5a411d111775e09db
Source dataset
uspto-grants-1988_09
Patent number
US04769386

Reaction notes

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