Tetrahydrofuran → HCID 70103189, compound

HRID 2393570Notes

Reaction equation

HRID 2393570 reaction equation
[CH2:1]([S:4][C:5]1[N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:7]([S:11][CH3:12])=[C:8](Br)[N:9]=1)[CH2:2][CH3:3].C1COCC1.C([Li])CCC.ClC(OCC)=O>CCCCCC.O>[CH2:1]([S:4][C:5]1[N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:18])[CH3:19])[C:7]([S:11][CH3:12])=[CH:8][N:9]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 70104303HCID 70104303, compoundHCID 178418339Butyllithium

Product 1

HCID 70103189HCID 70103189, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

7.94 g of the product obtained in Stage C above is introduced at ambient temperature into 80 cm3 of anhydrous THF, followed by cooling down to -78° C. and 13.75 cm3 of a 1.6M n-butyllithium solution in hexane is added. After 10 minutes, 15 cm3 of ethyl chloroformate is added, followed by agitation for another 15 minutes at -78° C. 60 cm3 of water is added, the reaction medium is left to return to ambient temperature, the THF is evaporated off, 10 cm3 of 32% soda is added to destroy the excess ethyl chloroformate, followed by extraction with 3×200 cm3 of AcOEt, washing with 2×80 cm3 of water, drying, filtering and evaporating.

Workup

  1. waitfollowed by agitation for another 15 minutes at -78° C
  2. waitthe reaction medium is left
  3. customto return to ambient temperature
  4. customthe THF is evaporated off
  5. addition10 cm3 of 32% soda is added
  6. customto destroy the excess ethyl chloroformate
  7. extractionfollowed by extraction with 3×200 cm3 of AcOEt
  8. washwashing with 2×80 cm3 of water
  9. customdrying
  10. filtrationfiltering
  11. customevaporating

Sources & evidence

ORD record
ord-293a73684e7d4982a53335e6257874c7
Source dataset
uspto-grants-1998_09
Patent number
US05807878

Reaction notes

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