Sodium hydride → Docos-21-yn-1-ol

HRID 2399981Notes

Reaction equation

HRID 2399981 reaction equation
NC(N)(C)C.[H-].[Na+].[CH2:8]([OH:30])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O>[CH2:8]([OH:30])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[CH:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 100948752,2-Propanediamine2×HCID 19385099Docos-12-ynol

Product 1

HCID 57307871Docos-21-yn-1-olYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diaminopropane (DAP) (150 ml) at room temperature under nitrogen was stirred and treated with sodium hydride (100%, 13.55 g, 0.56 mol). The resulting solution was then warmed to 70° C. for 1 hour after which time further DAP (30 ml) is added followed by docos-12-ynol (22 g, 0.068 mol). The resulting solution was then left at 70° C. overnight, cooled and poured into water. The aqueous mixture was extracted three times with chloroform, the combined organic dried (MgSO4), filtered and evaporated to leave a pinkish residue. Recrystallisation from methanol gave docos-21-ynol (31) (18.05 g, 84%) as white crystals mp 64°-70° C.

Workup

  1. additionis added
  2. temperaturecooled
  3. extractionThe aqueous mixture was extracted three times with chloroform
  4. dry with materialthe combined organic dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto leave a pinkish residue
  8. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-81c113d8701a4b2c931bfe570c19e3cd
Source dataset
uspto-grants-1995_09
Patent number
US05451691

Reaction notes

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