4-Nitrophenyl chloroformate → HCID 86712391, compound

HRID 1525625Notes

Reaction equation

HRID 1525625 reaction equation
[CH:1]1([O:9][CH2:10][CH2:11][OH:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]#[C:2]1.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>C1COCC1>[C:14](=[O:15])([O:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[O:12][CH2:11][CH2:10][O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]#[C:2]1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 867123901309581-54-1

Product 1

HCID 86712391HCID 86712391, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 10 (2.64 g, 15.7 mmol) and TEA (2.63 ml, 18.8 mmol 1.2 eq) dissolved in THF (0.2 M, 79 ml) were added dropwise to a stirred solution of 4-nitrophenyl chloroformate (9.49 g, 47.1 mmol, 3.0 eq) and THF (0.7 M, 22 ml) over a period of 1 h at −10° C. The reaction mixture was stirred overnight at RT and diluted with cHex (100 ml). Then cHex (100 ml) was added and the THF was removed under reduced pressure. Filtration of the reaction mixture followed by FC (cHex:EtOAc 4:1) gave compound 11 as a yellow oil (3.42 g, 10.3 mmol, 65%).

Workup

  1. additiondiluted with cHex (100 ml)
  2. additionThen cHex (100 ml) was added
  3. customthe THF was removed under reduced pressure
  4. filtrationFiltration of the reaction mixture

Sources & evidence

ORD record
ord-607b9d2219ca4ab28bce5d85c766acf1
Source dataset
uspto-grants-2015_07
Patent number
US09085514B2

Reaction notes

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