tert-Butanol → Tert-butyl n-(2-furyl)carbamate

HRID 2277128Notes

Reaction equation

HRID 2277128 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C(O)=O.C([N:11]([CH2:14]C)CC)C.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:17]C1C=CC=CC=1.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[NH:11][C:14](=[O:17])[O:39][C:35]([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 69192-Furancarboxylic acidHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azide

Product 1

HCID 317628Tert-butyl n-(2-furyl)carbamateYield 96%

Procedure

A solution of furan-2-carboxylic acid (35.0 g, 312.2 mmol), triethylamine (86 mL, 624.5 mmol), and diphenyl phosphorazidate (DPPA) (135 mL, 624.5 mmol) in tert-butyl alcohol (400 mL) was refluxed overnight. The volatile was removed in vacuo and the residue was purified by chromatography (silica gel, PE to EA:PE (1:30, v:v)) to give compound C3-2 as a white solid (55.0 g, yield: 96%). 1H NMR (DMSO-d6, 400 MHz) δ: 1.43 (s, 9H), 5.91 (s, 1H), 6.37 (t, J=2.6 Hz, 1H), 7.26 (s, 1H), 9.81 (s, 1H).

Workup

  1. customThe volatile was removed in vacuo
  2. customthe residue was purified by chromatography (silica gel, PE to EA:PE (1:30, v:v))

Sources & evidence

ORD record
ord-f9363078a2a443dc83df2e3b179ce116
Source dataset
uspto-grants-2015_09
Patent number
US09133161B2

Reaction notes

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