Acetic Anhydride → HCID 22036362, compound

HRID 493308Notes

Reaction equation

HRID 493308 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. additionwas added
  2. concentrationThe mixture was concentrated
  3. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d630742457bd4731bb09f6c254e43f8c
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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