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

HRID 390808

反応式

HRID 390808 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-49ff7c7182ce49f490840ef4883d3e93
出典データセット
uspto-grants-2013_02
特許番号
US08383620B2

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