Formaldehyde → HCID 69253409, compound

HRID 902758Notes

Reaction equation

HRID 902758 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=1)[C:6](=O)C(OCC)=O)[CH3:2].C=O.C(=O)([O-])[O-].[K+].[K+]>O.CCCCCC>[CH2:1]([O:3][C:4](=[O:27])[C:5]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=1)=[CH2:6])[CH3:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 69253905HCID 69253905, compound

Product 1

HCID 69253409HCID 69253409, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To 2-(3-Benzyloxy-phenyl)-3-oxo-succinic acid diethyl ester (1.28 g, 3.6 mmol) in water (5 ml) was added formaldehyde (600 uL, 37% solution, 6.6 mmol) and potassium carbonate (0.37 g, 2.7 mmol). The reaction was stirred vigorously overnight The organic products were extracted into diethyl ether which was dried (MgSO4), and evaporated. The residue was purified by column chromatography over silica gel (silica gel 60, EM Science) using 5% ethyl acetate:hexane as eluent to afford 0.99 g (55% yield) of the title compound as an oil. 1H NMR (CDCl3, 400 MHz) δ 7.48-7.27 (m, 6H), 7.10-6.97 (m, 3H), 6.35 (s, 1H), 5.90 (s, 1H), 5.10 (s, 2H), 4.30 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.2 Hz, 3H).

Workup

  1. extractionwere extracted into diethyl ether which
  2. dry with materialwas dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography over silica gel (silica gel 60, EM Science)

Sources & evidence

ORD record
ord-79d37bb8f81149d5973d80d61f36b164
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…