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Trityl chloride → Diethyl Ether

HRID 1914730
Notes
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Reaction equation

HRID 1914730 reaction equation
[O:1]=[C:2]1[C:10]2[NH:9][N:8]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:23]1([C:29](Cl)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[O:1]=[C:2]1[C:10]2[N:9]([C:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:8]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:11]([O:13][CH2:14][CH3:15])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178470478HCID 178470478, compound

Product 2

HCID 3283Diethyl EtherYield 874.2%HCID 68668650HCID 68668650, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

2.08 g (10.0 mmol) of ethyl 7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate were dissolved in 100 mL of dichloromethane and 0.76 mL of triethylamine and 3.07 g (11.0 mmol) of triphenylmethyl chloride were added. The solution was stirred at room temperature for 6 hours. Then the solution was further diluted with dichloromethane and washed with water. The organic layer was treated with anhydrous Na2SO4 and evaporated to dryness. The final product was obtained by crystallization from diethyl ether (3.24 g, 72% yield).

Workup

  1. washwashed with water
  2. additionThe organic layer was treated with anhydrous Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-d342f344adf64685abfcf473c402708d
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08614220B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes