Heptane → HCID 54144450, compound

HRID 488435Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:10][CH2:11][OH:12])=[CH:5][CH:4]=1.C(P(CCCC)CCCC)CCC.[CH3:34][O:35][C:36](=[O:50])[CH:37]([CH2:42][C:43]1[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=1)[C:38]([O:40][CH3:41])=[O:39].CCCCCCC>C1C=CC=CC=1>[CH3:41][O:40][C:38](=[O:39])[CH:37]([CH2:42][C:43]1[CH:44]=[CH:45][C:46]([O:12][CH2:11][CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:47][CH:48]=1)[C:36]([O:35][CH3:34])=[O:50]

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, 3,3-bis-(4-methoxy-phenyl)-prop-2-en-1-ol (500 mg, 1.95 mmol), tributylphosphine (424 (mg, 2.1 mmol) and 2-(4-hydroxy-benzyl)-malonic acid dimethyl ester (464 mg, 1.95 mmol) were successively dissolved in dry benzene (50 mL). Solid azodicarboxylic dipiperidide (ADDP) (530 mg, 2.1 mmol) was added under stirring at 0° C. to the solution. After 10 min, the reaction mixture was brought to room temperature and the stirring was continued for 16 h. Heptane (10 mL) was added to the reaction mixture and di hydro-ADDP separated out was filtered off. After evaporation of the solvent the product was purified by chromatography eluting with heptane/ethylacetate (4:1) to give 150 mg (16%) of the title compound.

Workup

customwas brought to room temperature
waitthe stirring was continued for 16 h
customseparated out
filtrationwas filtered off
customAfter evaporation of the solvent the product
customwas purified by chromatography
washeluting with heptane/ethylacetate (4:1)

Sources & evidence

ORD record: ord-0706d366b7f6418a985b51a2ed426acb
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972294B1

Reaction notes

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