Triethylamine → Benzyl 4-[6-(2,3-Dihydroxypropoxy)naphthalen-2-yl]but-3-ynylcarbamate

HRID 1644224Notes

Reaction equation

HRID 1644224 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[C:13][CH2:14][CH2:15][NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:6]=[CH:5]2.[O:27]1[CH2:29][CH:28]1[CH2:30][OH:31].C(N(CC)CC)C>CCO>[OH:27][CH:28]([CH2:30][OH:31])[CH2:29][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[C:13][CH2:14][CH2:15][NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11164GlycidolHCID 57828225Benzyl 4-(6-Hydroxynaphthalen-2-yl)but-3-ynylcarbamate

Product 1

HCID 57828252Benzyl 4-[6-(2,3-Dihydroxypropoxy)naphthalen-2-yl]but-3-ynylcarbamateYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(6-hydroxynaphthalen-2-yl)but-3-ynylcarbamate (30, 390 mg, 1.1 mmole), oxiran-2-ylmethanol (21, 0.1 mL, 1.4 mmole), and triethylamine (0.01 mL, 0.06 mmole) in absolute EtOH (8.8 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 carbamate 31 (236 mg, 42%) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.80 (s, 1H), 7.68 (dd, J=8.7, 3.9 Hz, 2H), 7.38-7.16 (m, 8H), 5.10 (s, 2H), 4.18 (dd, J=9.6, 4.2 Hz, 1H), 4.11-4.01 (m, 2H), 3.76-3.67 (m, 2H), 3.39-3.31 (m, 4H), 2.63 (t, J=6.9 Hz, 2H).

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-ce159c29e17a43ec95bc74c067fbff7a
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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