Diazomethane → HCID 57438380, compound

HRID 1818539Notes

Reaction equation

HRID 1818539 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[OH:7][C:8]1[C:9]([CH3:43])=[C:10]([CH:36]=[CH:37][C:38]=1[C:39](=[O:42])[CH2:40][CH3:41])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=2)C(O)=O)=[CH:15][CH:14]=1.[N+](=C)=[N-]>O1CCCC1.CN(C)C=O>[Cl:6][CH2:1][C:2]([C:22]1[CH:21]=[C:20]([CH:19]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[C:16]2[CH:15]=[CH:14][C:13]([CH2:12][O:11][C:10]3[CH:36]=[CH:37][C:38]([C:39](=[O:42])[CH2:40][CH3:41])=[C:8]([OH:7])[C:9]=3[CH3:43])=[CH:18][CH:17]=2)[CH:28]=[CH:27][CH:26]=1)=[O:3]

Participants

6

Reactant 3

HCID 9550DiazomethaneHCID 65578Oxalyl chlorideHCID 66699641HCID 66699641, compound

Product 1

HCID 57438380HCID 57438380, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add oxalyl chloride (0.660 mg, 5.20 mmol) to a solution of 3-[[4-(3-hydroxy-2-methyl-4-propionyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzoic acid (2.50 g, 5.00 mmol) in tetrahydrofuran (0.20M). Add dimethylformamide (5 drops). Add ethereal solution of diazomethane (15.0 mmol) and stir for 2 hours. Add hydrochloric acid (4N in dioxane) to quench unreacted diazomethane and evaporate solvents to afford the title compound (2.25 g, 4.19 mmol, 85%): MS (m/z): 536 (M−H).

Workup

  1. customAdd hydrochloric acid (4N in dioxane) to quench unreacted diazomethane
  2. customevaporate solvents

Sources & evidence

ORD record
ord-da80d598c8af4481bac72ed5e0433fe5
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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