3-Butenoic acid, 2,2-dimethyl- → HCID 86706143, compound

HRID 2176295Notes

Reaction equation

HRID 2176295 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH:5]([OH:10])[CH:6]1[CH2:9][O:8][CH2:7]1)[CH3:2].CC1C=CC=C([N+]([O-])=O)C=1C(OC(=O)C1C([N+]([O-])=O)=CC=CC=1C)=O.[CH3:37][C:38]([CH3:44])([CH:42]=[CH2:43])[C:39](O)=[O:40]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:3][C:4]([CH:5]([O:10][C:39](=[O:40])[C:38]([CH3:44])([CH3:37])[CH:42]=[CH2:43])[CH:6]1[CH2:7][O:8][CH2:9]1)=[O:11])[CH3:2]

Participants

6

Reactant 3

HCID 1391223-Butenoic acid, 2,2-dimethyl-HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 867061421509910-39-7

Product 1

HCID 86706143HCID 86706143, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of hydroxy-oxetan-3-yl-acetic acid ethyl ester (330 mg, 2.06 mmol), 2-methyl-6-nitrobenzoic anhydride (1.42 g, 4.12 mmol) and 4-dimethylamino pyridine (100 mg, 0.82 mmol) in dichloromethane (4 mL) was added a solution of 2,2-dimethyl-but-3-enoic acid (294 mg, 2.58 mmol) in dichloromethane (4 mL). The reaction mixture was stirred for 4 h and then evaporated. The residue was purified by silica gel chromatography using iso-hexanes/diethyl ether 4:1 to give the title compound (383 mg, 73%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.27 (t, J=7.1 Hz, 3H), 1.39 (s, 3H), 1.41 (s, 3H), 3.48-3.61 (m, 1H), 4.20 (q, J=7.1 Hz, 2H), 4.62-4.68 (m, 2H), 4.72-4.85 (m, 2H), 5.12-5.24 (m, 3H), 6.09 (dd, J=17.5, 10.6 Hz, 1H). LCMS (m/z) 257.1[M+H], Tr=2.31 min

Workup

  1. customevaporated
  2. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1573bed1fabd4d9093c7189e4ff53032
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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