Hexane → 2-Methoxy-8-triisopropylsilanyloxy-quinoxaline

HRID 1437374Notes

Reaction equation

HRID 1437374 reaction equation
[CH:1]([Si:4]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[NH:14][C:13](=[O:16])[CH:12]=[N:11]2)([CH3:3])[CH3:2].[CH2:23](N(CC)CC)C.C[Si](C=[N+]=[N-])(C)C.CCCCCC>ClCCl.CO.C(#N)C>[CH3:23][O:16][C:13]1[CH:12]=[N:11][C:10]2[C:15](=[C:6]([O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:17]([CH3:19])[CH3:18])[CH:20]([CH3:22])[CH3:21])[CH:7]=[CH:8][CH:9]=2)[N:14]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 167693TrimethylsilyldiazomethaneHCID 687012978-Triisopropylsilanyloxy-1H-quinoxalin-2-one

Product 1

HCID 686959212-Methoxy-8-triisopropylsilanyloxy-quinoxaline

Reagents, catalysts & solvents 1

HCID 22226298MeOH ACN DCMSolvent

Procedure

A solution of (c) (2.0 g, 6.2 mmol) in dichloromethane/methanol/acetonitrile (40 ml/4 ml/40 ml) was treated with triethylamine (1.1 ml, 8 mmol) then a solution of (trimethylsilyl)diazomethane in hexane (2M; 4 ml, 8 mmol). The mixture was stirred overnight then evaporated. The residue was chromatographed on silica eluting with dichloromethane affording an oil (1.0 g, 48%).

Workup

  1. customthen evaporated
  2. customThe residue was chromatographed on silica eluting with dichloromethane affording an oil (1.0 g, 48%)

Sources & evidence

ORD record
ord-ea157f6f8a0f4e7da2cdfde48cf12453
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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