Propargyl alcohol → HCID 10420045, compound

HRID 2213546Notes

Reaction equation

HRID 2213546 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C>CCOC(C)=O>[CH2:12]([O:15][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2)[C:13]#[CH:14]

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 791061-Bromoadamantane

Product 1

HCID 10420045HCID 10420045, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-bromoadamantane (10.8 g, 50.2 mmol), propargyl alcohol (30 ml, 515 mmol) and triethylamine (7.0 ml, 50.3 mmol) were heated at reflux for 4 hours. The reaction mixture was diluted with EtOAc (70 ml) and was washed sequentially with water (100 ml) and brine (100 ml). The organic phase was dried over magnesium sulfate and the filtrate was evaporated to give the title compound (9.64 g, 100%). 1H NMR (CDCl3) 4.14 (2H, d, J=2.4 Hz), 2.36 (1H, t, J=2.4), 2.16 (3H, s), 1.80-1.79 (6H, m), 1.67-1.57 (6H, m).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 4 hours
  3. washwas washed sequentially with water (100 ml) and brine (100 ml)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-fa6e4474b97745f7a46b359625c4319b
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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