Propargyl alcohol → HCID 21534973, compound

HRID 1657625Notes

Reaction equation

HRID 1657625 reaction equation
CN[C:3]([O:5][CH:6]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=O.[CH2:20](O)[C:21]#C>>[CH:18]1[C:19]2[CH:6]([O:5][CH2:3][C:20]#[CH:21])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:13][C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 7859Propargyl alcoholHCID 21482819HCID 21482819, compound

Product 1

HCID 21534973HCID 21534973, compound

Procedure

9-(N-Methylcarbamoyloxy)xanthene (3.0 g., 11.8 mmoles.) was stirred with 18 ml. of propargyl alcohol for 1.5 hours at room temperature, and the mixture was then filtered. The filtrate was evaporated in vacuo, and the residue was dissolved in ice-cold ether and washed twice with 20 ml. of ice-cold 10% aqueous acetic acid, 15 ml. of ice-cold water, and 10 ml. of ice-cold 5% aqueous sodium bicarbonate solution. After drying over potassium carbonate, the solvent was removed in vacuo. The resulting solid was recrystallized from hexane to give propargyl 9-xanthenyl ether, m.p. 74°-76°C.

Workup

  1. filtrationthe mixture was then filtered
  2. customThe filtrate was evaporated in vacuo
  3. dissolutionthe residue was dissolved in ice-cold ether
  4. washwashed twice with 20 ml
  5. dry with materialAfter drying over potassium carbonate
  6. customthe solvent was removed in vacuo
  7. customThe resulting solid was recrystallized from hexane

Sources & evidence

ORD record
ord-b51893dbd5cb4a639842ab720fecc0e7
Source dataset
uspto-grants-1976_06
Patent number
US03961069

Reaction notes

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