Tetrahydrofuran → HCID 13189273, compound

HRID 905020Notes

Reaction equation

HRID 905020 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.CC1C=CC(S(O[CH2:23][C@@H:24]([C@@H:39]2[C@:56]3([CH3:57])[C@H:42]([C@H:43]4[C@H:53]([CH2:54][CH2:55]3)[C@:51]3([CH3:52])[C:46]([CH2:47][C@@H:48]([O:65][CH:66]5[CH2:71][CH2:70][CH2:69][CH2:68][O:67]5)[CH2:49][C@@H:50]3[O:58][CH:59]3[CH2:64][CH2:63][CH2:62][CH2:61][O:60]3)=[CH:45][CH2:44]4)[CH2:41][CH2:40]2)[CH2:25][CH2:26][C:27]([F:38])([F:37])[C:28]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH3:29])(=O)=O)=CC=1>CCOCC>[O:60]1[CH2:61][CH2:62][CH2:63][CH2:64][CH:59]1[O:58][C@@H:50]1[C@@:51]2([CH3:52])[C:46](=[CH:45][CH2:44][C@@H:43]3[C@@H:53]2[CH2:54][CH2:55][C@@:56]2([CH3:57])[C@H:42]3[CH2:41][CH2:40][C@@H:39]2[C@H:24]([CH3:23])[CH2:25][CH2:26][C:27]([F:37])([F:38])[C:28]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH3:29])[CH2:47][C@@H:48]([O:65][CH:66]2[CH2:71][CH2:70][CH2:69][CH2:68][O:67]2)[CH2:49]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 13189269HCID 13189269, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13189273HCID 13189273, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 0.410 g (0.0108 mol) of lithium aluminum hydride, 50 mL of tetrahydrofuran and 2.98 g (0.0033 mol) of [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate) was heated at reflux (60°) for 1 hr and cooled to 0° C. The mixture was diluted with 120 mL of ether and quenched with the dropwise addition of 0.82 mL of water and 0.65 mL of 10% aqueous sodium hydroxide solution. The mixture was then dried for 1 hr and filtered. The solids were triturated with ether and filtered. The combined filtrates were evaporated to dryness and chromatographed on 0.06-0.20 mm silica gel to yield [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-ene, [α]D16 +2° (c 1, CHCl3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux (60°) for 1 hr
  3. customquenched with the dropwise addition of 0.82 mL of water and 0.65 mL of 10% aqueous sodium hydroxide solution
  4. customThe mixture was then dried for 1 hr
  5. filtrationfiltered
  6. customThe solids were triturated with ether
  7. filtrationfiltered
  8. customThe combined filtrates were evaporated to dryness
  9. customchromatographed on 0.06-0.20 mm silica gel

Sources & evidence

ORD record
ord-d04771fac0264f41a4984aaabb293bdf
Source dataset
uspto-grants-1983_12
Patent number
US04421690

Reaction notes

Loading…