Furfuryl Alcohol → HCID 25015138, compound

HRID 1915166Notes

Reaction equation

HRID 1915166 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][OH:26].CCOC(/N=N/C(OCC)=O)=O.O[C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[C:42](=[O:58])[N:43]([CH:50]1[CH2:55][CH2:54][C:53](=[O:56])[NH:52][C:51]1=[O:57])[C:44]2=[O:49]>C1COCC1.CO>[O:57]=[C:51]1[CH:50]([N:43]2[C:44](=[O:49])[C:45]3[C:41](=[CH:40][CH:48]=[CH:47][C:46]=3[O:26][CH2:25][C:21]3[O:20][CH:24]=[CH:23][CH:22]=3)[C:42]2=[O:58])[CH2:55][CH2:54][C:53](=[O:56])[NH:52]1

Participants

7

Reactant 4

HCID 7361Furfuryl AlcoholHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 117780874-Hydroxy thalidomide

Product 1

HCID 25015138HCID 25015138, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (630 mg, 2.4 mmol) and furan-2-yl-methanol (0.17 mL, 2.0 mmol) in THF (10 mL) was added a solution of DEAD (0.38 mL, 2.4 mmol) in THF (0.6 mL) at 0° C. After 5 min, 4-hydroxy-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (550 mg, 2.0 mmol) was added to the mixture. The mixture was allowed to warm to room temperature and kept for 4 h. The solvent was removed in vacuo, and the residue was purified by column chromatography (Silca Gel) to give an oil. The oil was slurried in methanol (10 mL) for 3 h to give a suspension. The suspension was filtered and washed with methanol (20 mL) to give 2-(2,6-dioxo-piperidin-3-yl)-4-(furan-2-ylmethoxy)-isoindole-1,3-dione as a yellow solid (310 mg, 44% yield): mp, 184-186° C.; 1H NMR (DMSO-d6) δ 1.99-2.04 (m, 1H, CHH), 2.42-2.61 (m, 2H, CH2), 2.80-2.95 (m, 1H, CHH), 5.07 (dd, J=5, 13 Hz, 1H, NCH), 5.35 (s, 2H, CH2), 6.49 (dd. J=2, 3 Hz, 1H, Ar), 6.68 (d. J=8 Hz, 1H, Ar), 7.47 (d, J=7 Hz, 1H, Ar), 7.68-7.71 (m, 2H, Ar), 7.83 (t J=8 Hz, 1H, Ar), 11.10 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.96, 30.93, 48.77, 62.55, 110.72, 111.38, 115.72, 116.64, 120.35, 133.35, 136.89, 143.99, 149.15, 155.12, 165.21, 166.73, 169.88, 172.76; Anal Calcd for C18H14N2O6+0.1H2O: C, 60.71; H, 4.02; N, 7.87; H2O, 0.51. Found: C, 60.47; H, 3.97; N, 7.73; H2O, 0.38.

Workup

  1. waitkept for 4 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography (Silca Gel)
  4. customto give an oil
  5. customto give a suspension
  6. filtrationThe suspension was filtered
  7. washwashed with methanol (20 mL)

Sources & evidence

ORD record
ord-7ee7e57f6811447497cbd9e2c47176f3
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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