Water → HCID 19967155, compound

HRID 976347Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]#[C:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1.[CH:22]([C:24]1[C:25]([OH:38])=[CH:26][C:27]2[C:28]([CH3:37])([CH3:36])[CH2:29][CH2:30][C:31]([CH3:35])([CH3:34])[C:32]=2[CH:33]=1)=[O:23].O>CN(C)C=O>[CH:22]([C:24]1[C:25]([O:38][CH2:8][C:9]#[C:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)=[CH:26][C:27]2[C:28]([CH3:37])([CH3:36])[CH2:29][CH2:30][C:31]([CH3:34])([CH3:35])[C:32]=2[CH:33]=1)=[O:23]

Participants

Conditions

Temperature: 50 °C

Procedure

0.71 g of potassium carbonate and 1.0 g of ethyl 4-(3-bromo-1-propynyl)benzoate were added to 20 ml of a solution of 0.80 g of 3-formyl-5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene in anhydrous N,N-dimethyl formamide at room temperature. The obtained mixture was stirred at 50° C. for 30 minutes, followed by the addition thereto of 20 ml of water. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography (developer: 20% diethyl ether/n-hexane) to give 0.87 g of the title compound as a pale-yellow solid.

Workup

additionfollowed by the addition
extractionThe obtained mixture was extracted with ethyl acetate
washThe organic phase was washed with a saturated aqueous solution of common salt
dry with materialdried over anhydrous magnesium sulfate
distillationdistilled
customto remove the solvent
customThe residue was purified by silica gel chromatography (developer: 20% diethyl ether/n-hexane)

Sources & evidence

ORD record: ord-095ac50d416548adb3a5daf3f6b38916
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612356

Reaction notes

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