Dichloromethane → HCID 10151049, compound

HRID 898657Notes

Reaction equation

HRID 898657 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:17]([OH:19])=[O:18])[CH:6]=[C:7]2[C:12]=1[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]2([CH3:16])[CH3:15])#[CH:2].ClCCl.Cl.CN(C)CCCN=C=NCC.[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36].[CH3:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>CN(C)C1C=CN=CC=1>[CH2:39]([O:38][C:35]([CH2:36][C:43]1[CH:42]=[CH:41][C:46]([O:18][C:17]([C:5]2[CH:6]=[C:7]3[C:12](=[C:3]([C:1]#[CH:2])[CH:4]=2)[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]3([CH3:15])[CH3:16])=[O:19])=[CH:45][CH:44]=1)=[O:37])[CH3:40]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12137002HCID 12137002, compound2×

Product 1

HCID 10151049HCID 10151049, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Following General Procedure D and using 8-ethynyl-2,2,4,4-tetramethyl chroman-6-carboxylic acid (Compound 26, 0.45 g, 1.75 mmol), anhydrous dichloromethane (20 mL), ethyl-4-hydroxy phenyl acetate (Compound 15, 0.38 g, 2.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.5 g, 2.62 mmol) and 4-(dimethylamino)pyridine (0.43 g, 3.5 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 20% ethyl acetate in hexane as the eluent, the title compound was obtained as white solid (0.536 g, 74%).

Sources & evidence

ORD record
ord-e1214d1bbc594260b4b33991050f8dd6
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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