Acetic Anhydride → HCID 22036362, compound

HRID 1789722Notes

Reaction equation

HRID 1789722 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH:15]([CH2:18][OH:19])[O:14][C:13]=2[CH:20]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH:15]([CH2:18][OH:19])[O:14][C:13]=2[CH:20]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 22036433(7-Amino-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

Product 1

HCID 22036362HCID 22036362, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.24 g, 2.4 mmol) was added to a stirred mixture of the title compound from Step 1 above (0.30 g, 1.66 mmol) and Et3N (0.70 g, 6.9 mmol) in CH2Cl2(30 mL). The reaction was stirred at room temperature for 15 h. More acetic anhydride (0.10 g, 1.0 mmol) was added and the mixture was stirred for a further 5 h at room temperature. The mixture was concentrated and the residue purified by chromatography on silica gel using EtOAc/isohexane (1:3 to 2:3) as eluent to give 170 mg (46%) of the title product as an oil.

Workup

  1. stirringthe mixture was stirred for a further 5 h at room temperature
  2. concentrationThe mixture was concentrated
  3. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8b94bdbb09c74fa7bcbd2c63cdf905eb
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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