Hydrochloric Acid → HCID 58378341, compound

HRID 2194551Notes

Reaction equation

HRID 2194551 reaction equation
[CH2:1]([OH:6])[CH2:2][CH:3](C)C.[C:7](Cl)(=[O:18])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.N1C(C)=CC(C)=C[C:21]=1C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:7](=[O:18])([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[O:6][CH:1]([CH2:2][CH3:3])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 31260Isoamyl AlcoholHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 58378341HCID 58378341, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of isoamyl alcohol (1.0 g, 13.5 mmol) in CH2Cl2 (30 ml) is added 4-nitrophenyl carbonochloridate (3.2 g, 16.2 mmol), 2,4,6-collidine (2.14 ml, 16.2 mmol) and a catalytic amount of DMAP. After stirring for 2 h, 1N HCl is added and the aqueous layer is extracted with CH2Cl2, and the combined organic layers washed with 1N HCl, brine, and dried over Na2SO4. Evaporation of solvent and purification by flash chromatography (120 g SiO2, EtOAc/hexanes gradient) yields sec-butyl 4-nitrophenyl carbonate F5a as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ=8.27 (d, J=9.2 Hz, 2H), 7.38 (d, J=9.2 Hz, 2H), 4.85 (sextet, J=6.4 Hz, 1H), 1.82-1.62 (m, 2H), 1.37 (d, J=6.4 Hz, 3H), 1.00 (t, J=7.2 Hz, 3H); MS calcd. for [M+Na]+C11H13NaNO5: 262.1. found: 262.2.

Workup

  1. extractionthe aqueous layer is extracted with CH2Cl2
  2. washthe combined organic layers washed with 1N HCl, brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of solvent and purification by flash chromatography (120 g SiO2, EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-92de611a57d94472b84d9807aa00c26e
Source dataset
uspto-grants-2012_12
Patent number
US08334288B2

Reaction notes

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