Tetrahydrofurfuryl alcohol → HCID 23286429, compound

HRID 1109245Notes

Reaction equation

HRID 1109245 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][O:4]1.C(N(CC)CC)C.[Br:15][CH:16]([CH3:20])[C:17](Cl)=[O:18]>C(OCC)C>[Br:15][CH:16]([CH3:20])[C:17]([O:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][O:4]1)=[O:18]

Participants

5

Reactant 3

HCID 7360Tetrahydrofurfuryl alcoholHCID 8471TriethylamineHCID 979802-Bromopropanoyl chloride

Product 1

HCID 23286429HCID 23286429, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 250 milliliter three-necked flask were added 0.15 mole of 2-(hydroxymethyl)tetrahydrofuran, 0.15 mole of triethylamine, and 100 milliliters of diethylether. The flask was immersed in ice, and 0.15 mole of 2-bromopropanoyl chloride introduced dropwise. The ice bath was removed, and the reaction stirred at ambient temperature for two hours. The mixture was extracted with an equal volume of water, and the organic phase dried over sodium sulfate. Decantation and solvent removal resulted in 2-tetrahydrofuranylmethyl 2-bromopropanoate in 94% yield.

Workup

  1. customThe ice bath was removed
  2. extractionThe mixture was extracted with an equal volume of water
  3. dry with materialthe organic phase dried over sodium sulfate
  4. customDecantation and solvent removal
  5. customresulted in 2-tetrahydrofuranylmethyl 2-bromopropanoate in 94% yield

Sources & evidence

ORD record
ord-ff7be6a7a0be403a8d8ff12142ee2ad3
Source dataset
uspto-grants-1994_06
Patent number
US05319102

Reaction notes

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