O-Xylene → HCID 13189280, compound

HRID 745647Notes

Reaction equation

HRID 745647 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:32]2([CH3:33])[C:9](=[CH:10][CH:11](Br)[C@@H:12]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:34])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:27])[CH2:18][CH2:19][C:20]([F:26])([F:25])[C:21]([OH:24])([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[CH2:6]1)(=[O:3])[CH3:2].CC1C=C(C)N=C(C)C=1.C1(C)C(C)=CC=CC=1>C1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@:32]2([CH3:33])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:34])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:27])[CH2:18][CH2:19][C:20]([F:26])([F:25])[C:21]([OH:24])([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 79532,4,6-TrimethylpyridineHCID 13189277HCID 13189277, compound

Product 1

HCID 13189280HCID 13189280, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1.33 g (0.0019 mol) of [1α,3β,7ξ]-7-bromo-24,24-difluorocholest-5-en-1,3,25-triol 1,3-diacetate, 0.8 mL of s-collidine and 10 mL of xylene was heated at reflux (140° C.) for 0.5 hr and cooled. The mixture was diluted with 30 mL of benzene. This solution was washed with 10% aqueous sulfuric acid, and saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The residue was purified by column chromatography on 0.06-0.20 mm silica gel to yield [1α,3β]-24,24-difluorocholesta-5,7-dien-1,3,25-triol 1,3-diacetate, [α]D25 -31° (c 0.4, CHCl3), mp 130°-132°. UV max (C2H5OH) 261 (ε 7750), 270 (ε 11,200), 281 (ε 12,100) and 293 (ε 7100).

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. washThis solution was washed with 10% aqueous sulfuric acid, and saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on 0.06-0.20 mm silica gel

Sources & evidence

ORD record
ord-96fe0efd1b7d4599b010d530a0c1702f
Source dataset
uspto-grants-1986_07
Patent number
US04599330

Reaction notes

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