Dichloromethane → HCID 66593487, compound

HRID 1092376Notes

Reaction equation

HRID 1092376 reaction equation
C(Cl)Cl.[C:4]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)([CH3:7])([CH3:6])[CH3:5].[C:15](=O)([O:26]C1C=CC([N+]([O-])=O)=CC=1)[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.CCCCCC.C(OC(=O)C)C>[C:15](=[O:26])([O:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:4]([CH3:7])([CH3:5])[CH3:6])[CH:9]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 78756Bis(4-nitrophenyl) carbonate

Product 1

HCID 66593487HCID 66593487, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

An oven-dried 25 mL flask was charged with dry CH2Cl2 (5 mL), 3-t-butylphenol (100 mg, 0.67 mmol), bis(4-nitrophenyl) carbonate (405 mg, 1.34 mmol) and 4-DMAP (162 mg, 1.34 mmol). The reaction was stirred overnight at room temperature and then evaporated. Column chromatography (n-hexane/ethylacetate 8:1) yielded 3-t-butylphenyl 4-nitrophenyl carbonate (189 mg, 0.60 mmol, 90%). This carbonate was dissolved in dry CH2Cl2 (8 mL) and 4-DMAP (162 mg, 1.34 mmol) was added. After 15 min, propargylamine (73 mg, 0.085 ml, 1.34 mmol) was added by syringe. The reaction was allowed to stir overnight at room temperature and then evaporated. Column chromatography (n-hexane/ethylacetate 15:1) yielded N-propargyl-3-t-butylphenyl carbamate (93 mg, 0.40 mmol, 60%). 1H NMR (CDCl3, 400 MHz) δ 1.32 (t, 9H), 2.30 (s, 1H), 4.08 (d, J=5.2 Hz, 2H), 5.27 (broad, 1H), 6.97 (d, J=7.2 Hz, 1H), 7.13 (d, J=2.0 Hz, 1H), 7.23˜7.31 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 30.9, 31.2, 34.7, 72.0, 79.3, 118.5, 122.5, 128.8, 150.6, 152.9, 154.2.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-45aad9164a5b42a0bc4b0ff03b9ae901
Source dataset
uspto-grants-2012_03
Patent number
US08129428B2

Reaction notes

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