Glycidol → HCID 57828215, compound

HRID 1644218Notes

Reaction equation

HRID 1644218 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[O:27]1[CH2:29][CH:28]1[CH2:30][OH:31]>CCO.C(N(CC)CC)C>[OH:27][CH:28]([CH2:30][OH:31])[CH2:29][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11164GlycidolHCID 57828216HCID 57828216, compound

Product 1

HCID 57828215HCID 57828215, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 4-(4-hydroxynaphthalen-1-yl)butylcarbamate (20, 287 mg, 0.82 mmole), oxiran-2-ylmethanol (21, 0.07 mL, 1.00 mmole) and triethylamine (0.01 mL, 0.05 mmole) in absolute EtOH (9.28 mL) was subjected to microwave irradiation at 130° C. for 30 min. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silical gel, 95:5 CH2Cl2/MeOH) to afford butylcarbamate 22 (293 mg, 83%) as a light yellow thick oil: 1H NMR (300 MHz, CDCl3) δ 8.24 (d, J=7.7 Hz, 1H), 7.94 (d, J=8.1 Hz, 1H), 7.52-7.45 (m, 2H), 7.37 7.28 (m, 5H), 7.18 (d, J=7.7 Hz, 1H), 6.75 (d, J=8.0 Hz, 1H), 5.09 (br s, 2H), 4.71 (br s, 1H), 4.29-4.20 (m, 3H), 3.98-3.81 (m, 2H), 3.23 (q, J=6.5 Hz, 2H), 3.00 (t, J=7.5 Hz, 2H), 2.65 (d, J=4.5 Hz, 1H), 2.06 (t, J=5.8 Hz, 1H), 1.83-1.53 (m, 4H).

Workup

  1. customirradiation at 130° C. for 30 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography (silical gel, 95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-6e6516b60db9451fb1d00a1ec4205af0
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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