Aluminium lithium hydride → HCID 71570849, compound

HRID 578746Notes

Reaction equation

HRID 578746 reaction equation
[C:1]1([CH:7]2[O:14][CH2:13][C@H:12]3[C@:10]([C:15](OCC)=[O:16])([CH2:11]3)[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([CH:7]2[O:14][CH2:13][C@H:12]3[C@:10]([CH2:15][OH:16])([CH2:11]3)[CH2:9][O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 89569177HCID 89569177, compound

Product 1

HCID 71570849HCID 71570849, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
12.5 °C

Procedure

In a reactor, tetrahydrofuran (110.0 L) was charged under nitrogen, followed by addition of ethyl (1R,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octane-1-carboxylate (11.0 kg, 41.9 mol). The mixture was stirred to get a clear solution and cooled to 10-15° C. Lithium aluminium hydride (2 M in tetrahydrofuran, 17.1 L, 35.6 mol) was added drop wise over a period of 1 hour by maintaining the temperature at 10-15° C. The progress of the reaction was monitored by HPLC. After completion of the reaction, the reaction mass was cooled to 0-5° C. and quenched with subsequent addition of ethyl acetate (55.0 L) and brine (55.0 L) maintaining that temperature. The temperature of the reaction mass was gradually raised to 20-25° C. and stirred for 1 h. The organic layer was separated and washed with water (55.0 L) and brine (55.0 L). The organic layer was dried over sodium sulfate (6.0 kg) and the solvent was distilled off. Petroleum ether (22.0 L) was added to the residue to precipitate the product and the slurry was cooled to 0-5° C. and stirred for 30 min. The slurry was filtered and washed with cold petroleum ether (5.0 L). The product was dried in a vacuum tray dryer for 4 hours below 40-45° C. to afford 7.6 Kg of the title compound (5c) as crude product.

Workup

  1. customto get a clear solution
  2. temperatureby maintaining the temperature at 10-15° C
  3. customAfter completion of the reaction
  4. temperaturethe reaction mass was cooled to 0-5° C.
  5. customquenched with subsequent addition of ethyl acetate (55.0 L) and brine (55.0 L)
  6. temperaturemaintaining that temperature
  7. temperatureThe temperature of the reaction mass was gradually raised to 20-25° C.
  8. stirringstirred for 1 h
  9. customThe organic layer was separated
  10. washwashed with water (55.0 L) and brine (55.0 L)
  11. dry with materialThe organic layer was dried over sodium sulfate (6.0 kg)
  12. distillationthe solvent was distilled off
  13. additionPetroleum ether (22.0 L) was added to the residue
  14. customto precipitate the product
  15. temperaturethe slurry was cooled to 0-5° C.
  16. stirringstirred for 30 min
  17. filtrationThe slurry was filtered
  18. washwashed with cold petroleum ether (5.0 L)
  19. customThe product was dried in a vacuum tray dryer for 4 hours below 40-45° C.

Sources & evidence

ORD record
ord-00fdf06429534a439bdbaa62ee127627
Source dataset
uspto-grants-2015_05
Patent number
US09040699B2

Reaction notes

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