Sodium Chloride → HCID 53818145, compound

HRID 53452Notes

Reaction equation

HRID 53452 reaction equation
[CH2:1]1[O:31][C:30]2[CH:29]=[CH:28][C:5]([C:6]([C@H:8]3[CH2:13][CH2:12][C@H:11]4[C@H:14]5[C@H:23]([CH2:24][CH2:25][C@:9]34[CH3:10])[C:22]3[CH:21]=[CH:20][C:19]([CH:26]=[O:27])=[CH:18][C:17]=3[CH2:16][CH2:15]5)=[O:7])=[CH:4][C:3]=2[O:2]1.CC(=CC)C.[O-:37]Cl=O.[Na+].[Na+].[Cl-]>O.C(O)(=O)C.C(O)(C)(C)C>[CH2:1]1[O:31][C:30]2[CH:29]=[CH:28][C:5]([C:6]([C@H:8]3[CH2:13][CH2:12][C@H:11]4[C@H:14]5[C@H:23]([CH2:24][CH2:25][C@:9]34[CH3:10])[C:22]3[CH:21]=[CH:20][C:19]([C:26]([OH:37])=[O:27])=[CH:18][C:17]=3[CH2:16][CH2:15]5)=[O:7])=[CH:4][C:3]=2[O:2]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 8675069717beta-(3,4-Methylenedioxybenzoyl)-estra-1,3,5(10)-triene-3-carboxaldehyde

Product 1

HCID 53818145HCID 53818145, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a stirred mixture of 17β-(3,4-methylenedioxybenzoyl)-estra-1,3,5(10)-triene-3-carboxaldehyde (0.041 g, 0,1 mmoles), tert-butyl alcohol (1.05 mL), 2-methyl-2-butene (4 mL of 2M solution in THF, 8 mmoles) at 0° C. was added a solution of NaClO2 (9 mg, 0.1 mmoles) and NaH2PO4. H2O (0.137 g, 0.1 mmoles) in H2O (0.4 ml) and stirred for 2 hours at ambient temperature. Acetic acid (glacial, 0.8 ml) and saturated NaCl solution (1.3 mL) were added to the reaction mixture which was extracted with EtOAc. The organic layer was washed with H2O, brine, dried (MgSO4), concentrated and azetroped with toluene. The resulting solid was triturated with CH3CN- acetone and filtered to give 0.02 g (47%) of the title compound as a white solid, mp 235°-237° C.

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated and azetroped with toluene
  5. customThe resulting solid was triturated with CH3CN- acetone
  6. filtrationfiltered

Sources & evidence

ORD record
ord-445fe49cda48466b98b98166a74cd334
Source dataset
uspto-grants-1997_04
Patent number
US05618806

Reaction notes

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