Diisobutylaluminumhydride → HCID 57311870, compound

HRID 256227Notes

Reaction equation

HRID 256227 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:23])[C@H:17]2[C@@H:13]1[C@H:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[O:15][C:16]2=[O:18]>C1(C)C=CC=CC=1>[CH3:11][C:12]1([CH3:23])[C@H:17]2[C@@H:13]1[C@H:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[O:15][C@H:16]2[OH:18]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 70431262HCID 70431262, compound

Product 1

HCID 57311870HCID 57311870, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

15.5 ml of a toluene solution of 20% of diisobutyl aluminum hydride were slowly added at -70° C. to a solution of 2.5 g of the product of Step B in 25 ml of toluene with stirring and the mixture was poured over ice. The mixture was filtered and the filtrate was extracted with ether and was evaporated to dryness under reduced pressure to obtain 2.5 g of (1R,2R,4R,5S) 6,6-dimethyl-4-(2-methyl-prop-2-yl)-3-oxa-bicyclo(3,1,0)hexan-2-ol melting at 126° C.

Workup

  1. additionthe mixture was poured over ice
  2. filtrationThe mixture was filtered
  3. extractionthe filtrate was extracted with ether
  4. customwas evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1504d2d1bed746f380f3cee6bf2c2d07
Source dataset
uspto-grants-1987_10
Patent number
US04701542

Reaction notes

Loading…