Triethylamine → HCID 54300837, compound

HRID 848949Notes

Reaction equation

HRID 848949 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].C(N(CC)CC)C.[C:14]12([C:24](Cl)=[O:25])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2>C1COCC1.C(OCC)(=O)C>[C:14]12([C:24]([O:5][CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])=[O:25])[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 111733-Methyl-2-buten-1-OLHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 54300837HCID 54300837, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A flask was charged with 2.6 g (0.03 mol) of 3-methyl-2-buten-1-ol, 3.1 g (0.025 mol) of triethylamine and 20 ml of THF to prepare a solution. While stirring the solution, a solution of 5.0 g (0.025 mol) of 1-adamantanecarbonyl chloride in 40 ml of THF was added dropwise over 1 hour, followed by stirring further for 5 hours. After salts formed were removed by filtration from the reaction mixture, the filtrate was concentrated. The thus-obtained crude product was dissolved in 70 ml of ethyl acetate, and the solution was washed each 3 times with a 5% aqueous solution of sodium hydrogencarbonate and saturated saline and dried over magnesium sulfate. The solvent was then distilled off to obtain 4.9 g of 3-methyl-2-butenyl 1-adamantanecarboxylate [the formula (61)].

Workup

  1. customto prepare a solution
  2. stirringby stirring further for 5 hours
  3. customAfter salts formed
  4. customwere removed by filtration from the reaction mixture
  5. concentrationthe filtrate was concentrated
  6. customThe thus-obtained crude product
  7. washthe solution was washed each 3 times with a 5% aqueous solution of sodium hydrogencarbonate and saturated saline
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-ddf9d4e7a8ea4677b4104000b9c30a15
Source dataset
uspto-grants-2000_01
Patent number
US06010826

Reaction notes

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