Triethylamine → HCID 12854480, compound

HRID 1074902Notes

Reaction equation

HRID 1074902 reaction equation
[OH:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]([CH2:12][OH:13])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>O1CCCC1>[CH2:25]([O:24][C:22]([O:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]([CH2:12][OH:13])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12854479HCID 12854479, compound

Product 1

HCID 12854480HCID 12854480, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

23.95 g of 3,4-dihydro-8-hydroxy-3-hydroxymethyl-2H-1-benzopyran was dissolved in 270 ml of tetrahydrofuran, and 14.8 g of triethylamine was added. With stirring under ice cooling, a solution of 15.9 g of ethyl chloroformate in 135 ml of tetrahydrofuran was added dropwise over 1.5 hours. The mixture was stirred at 2° C. for 1.5 hours. After the reaction, the insoluble matter was removed by filtration, and the mother liquor was distilled under reduced pressure. To the residue was added 500 ml of ethyl acetate to form a solution. The solution was washed successively with 2 N hydrochloric acid and a saturated aqueous solution of sodium chloride, and dried. The solvent was distilled off to give 33.6 g (yield 100%) of 3,4-dihydro-8-ethoxycarbonyloxy-3-hydroxymethyl-2H-1-benzopyran.

Workup

  1. stirringThe mixture was stirred at 2° C. for 1.5 hours
  2. customAfter the reaction
  3. customthe insoluble matter was removed by filtration
  4. distillationthe mother liquor was distilled under reduced pressure
  5. additionTo the residue was added 500 ml of ethyl acetate
  6. customto form a solution
  7. washThe solution was washed successively with 2 N hydrochloric acid
  8. dry with materiala saturated aqueous solution of sodium chloride, and dried
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-b0195f00d9db464aade408a07d3e54ba
Source dataset
uspto-grants-1983_07
Patent number
US04394382

Reaction notes

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