4-Nitrophenol → HCID 67125498, compound

HRID 920607Notes

Reaction equation

HRID 920607 reaction equation
[F:1][CH:2]([F:21])[O:3][C:4]1[C:9]2[O:10][C:11]3([O:17][C:8]=2[C:7]([C:18]([OH:20])=[O:19])=[CH:6][CH:5]=1)[CH2:16][CH2:15][S:14][CH2:13][CH2:12]3.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23].COC(C)(C)C.CCOC(C)=O>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:21][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3([O:17][C:8]=2[C:7]([C:18]([O:20][C:28]2[CH:29]=[CH:30][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)=[O:19])=[CH:6][CH:5]=1)[CH2:16][CH2:15][S:14][CH2:13][CH2:12]3

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 8857Ethyl AcetateHCID 15413tert-Butyl methyl etherHCID 67125523HCID 67125523, compound

Product 1

HCID 67125498HCID 67125498, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

7-Difluoromethoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylic acid (344 mg) was dissolved in dry DMF (3 mL). 4-Nitrophenol (226 mg) Ethyl-dimethylaminopropylcarbodiimide hydrochloride (312 mg) and N,N-Dimethyl-4-aminopyridine (198 mg) was added. After stirring at room temperature for 20 hours, aqueous work up with tert-Butyl methyl ether and chromatography of the organics in a gradient from 0 to 40% EtOAc in pentanes afforded the title compound as an oil.

Sources & evidence

ORD record
ord-69c5ad80798140938b55321140caf01d
Source dataset
uspto-grants-2016_03
Patent number
US09273064B2

Reaction notes

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