tert-Butanol → tert-butyl N-(furan-3-yl)carbamate

HRID 390808

Reaction equation

HRID 390808 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](C(O)=O)=[CH:2]1.C([N:11]([CH2:14]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])C=CC=CC=1.[C:33]([OH:37])([CH3:36])([CH3:35])[CH3:34]>>[O:1]1[CH:5]=[CH:4][C:3]([NH:11][C:14](=[O:23])[O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:2]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 102683-Furoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 12207186tert-butyl N-(furan-3-yl)carbamateYield 76%

Procedure

3-Furoic acid (5.60 g, 1.0 eq) was dissolved in tert-butanol (200 ml) and treated with triethylamine (10 ml, 1.4 eq) and diphenyl phosphoryl azide (12 ml, 1.1 eq). Mixture was heated at reflux for 18 h. Reaction mixture was cooled to room temperature, then concentrated to 50 ml and poured into saturated aq. NaHCO3. Mixture was stirred at 0° C. for 2 h. Solid was collected by filtration and dried under high vacuum. The crude reaction mixture was purified by flash chromatography to yield tert-butyl furan-3-ylcarbamate 32 (6.95 g, 76%): 1H NMR (CDCl3, 400 MHz) δ 7.71 (bs, 1H), 7.27 (m, 1H), 6.27 (bs, 1H), 6.20 (bs, 1H), 1.50 (s, 9H); MS (Q1) 184 (M)+.

Workup

  1. temperatureMixture was heated
  2. temperatureat reflux for 18 h
  3. customReaction mixture
  4. concentrationconcentrated to 50 ml
  5. additionpoured into saturated aq. NaHCO3
  6. filtrationSolid was collected by filtration
  7. customdried under high vacuum
  8. customThe crude reaction mixture
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-49ff7c7182ce49f490840ef4883d3e93
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Linked notes

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