Hydrochloric Acid → HCID 15671158, compound

HRID 2351518Notes

Reaction equation

HRID 2351518 reaction equation
C([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9](=[O:28])[CH2:10][C:11]([CH3:27])([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([N+]([O-])=O)=[CH:20][CH:19]=3)[O:12]2)=[CH:7][C:6]=1[C:29](=[O:31])[CH3:30])(=O)C.N([O-])=O.[Na+].[ClH:36].[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH:38]=[CH2:39]>[Pd].O.CC(C)=O.C1C=CC=CC=1.CO>[C:29]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH3:15])[C:5]=1[OH:4])[O:12][C:11]([CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:39][CH:38]([Cl:36])[C:37]([O:41][CH2:42][CH3:43])=[O:40])=[CH:22][CH:23]=1)([CH3:27])[CH2:10][C:9]2=[O:28])(=[O:31])[CH3:30]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 15671157HCID 15671157, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15671158HCID 15671158, compound

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following a procedure similar to that described in Preparation 4, 0.8 g of 7-acetoxy-6-acetyl-2,8-dimethyl-2-(4-nitrophenoxymethyl)-4-oxochroman (prepared as described in Preparation 22) was hydrogenated by using 0.2 g of 10% w/w/ palladium-on-carbon, 8 ml of methanol and 1 ml of benzene. The product was then reacted with 135 mg of sodium nitrite, 0.6 ml of concentrated aqueous hydrochloric acid, 1.6 ml of ethyl acrylate, 30 mg of cuprous oxide, 6 ml of acetone and 0.5 ml of water, following a procedure similar to that described in Preparation 5, to give the title compound in admixture with its 7-acetoxy compound in a ratio of about 1:1. The mixture was subjected to silica gel column chromatography eluted with a 10:1 by volume mixture of benzene and ethyl acetate, to afford the title compound as a pale yellow oily substance.

Workup

  1. customthat described in Preparation 5

Sources & evidence

ORD record
ord-7d7c5022388a44368259416b6d5837e6
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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