Triethyl orthoacetate → HCID 68312936, compound

HRID 1843128Notes

Reaction equation

HRID 1843128 reaction equation
O=[C:2]1[N:21]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2=[N:6][C:7]([C:10]3[CH:11]=[N:12][N:13]4[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=34)=[CH:8][CH:9]=[C:4]2[NH:3]1.[C:28](OCC)(OCC)(OCC)C.C(Cl)Cl.CO>CCO>[CH3:28][C:2]1[N:21]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2=[N:6][C:7]([C:10]3[CH:11]=[N:12][N:13]4[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=34)=[CH:8][CH:9]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 66221Triethyl orthoacetateHCID 21226129Dichloromethane methanolHCID 67123825HCID 67123825, compound

Product 1

HCID 68312936HCID 68312936, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of the compound obtained in example 2 section d (56.4 mg, 0.169 mmol) in EtOH (1.5 mL), PTSA monohydrate (3.21 mg, 0.017 mmol) and triethyl orthoacetate (547 mg, 3.37 mmol) were added. The reaction mixture was heated in a CEM Explorer microwave oven at 145° C. and 270 W for 2.5 hours. The crude residue was cromategraphed on a silica gel flash system (ISCO Rf) using CH2Cl2/MeOH mixtures of increasing polarity, a eluent to afford the desired product (15% yield).

Workup

  1. temperatureof increasing polarity

Sources & evidence

ORD record
ord-cc92f0400ad646e396c2a7e312c59a9b
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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