Triethyl orthoacetate → HCID 59560314, compound

HRID 1177346Notes

Reaction equation

HRID 1177346 reaction equation
[C:1](OCC)(OCC)(OCC)[CH3:2].Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([OH:25])[C:23]=1[OH:24])[C:17]([O:19][CH3:20])=[O:18]>CCCCCC>[OH:25][C:22]1[C:23]2[O:24][C:1]([CH3:2])=[N:13][C:14]=2[CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[CH:21]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 44203162HCID 44203162, compound

Product 1

HCID 59560314HCID 59560314, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To stirred triethyl orthoacetate (35.0 mL, 190 mmol) was added methyl 3-amino-4,5-dihydroxybenzoate hydrochloride (6.00 g, 27.3 mmol). The stirred suspension was refluxed for 20 min and cooled to room temperature. The reaction mixture was poured into hexane (200 mL). The formed precipitate was separated by filtration and vacuum-dried to afford the desired benzoxazole (4.98 g, 24.04 mmol, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.74 (br. s, 1H), 7.66 (d, J=1.4 Hz, 1H), 7.43 (d, J=1.4 Hz, 1H), 3.85 (s, 3H), 2.62 (s, 3H).

Workup

  1. temperatureThe stirred suspension was refluxed for 20 min
  2. customThe formed precipitate was separated by filtration
  3. customvacuum-dried

Sources & evidence

ORD record
ord-1efc0d7296b74a4c850a2bb1d7b42043
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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