O-Xylene → HCID 13189280, compound

HRID 905023Notes

Reaction equation

HRID 905023 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 (ε7750), 270 (ε11,200), 281 (ε12,100) and 293 nm (ε7100).

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-62e419ad1d6d492396feac5f69ccd762
Source dataset
uspto-grants-1983_12
Patent number
US04421690

Reaction notes

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