Diisobutylaluminumhydride → HCID 11631210, compound

HRID 1987534Notes

Reaction equation

C[O:2][C:3]([C:5]1[C@H:9]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7][CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[C:21]1([CH2:20][O:19][C@@H:8]2[C@@H:9]([CH2:10][O:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:5]([CH2:3][OH:2])=[CH:6][CH2:7]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a round bottomed flask equipped with an argon inlet, magnetic stirrer and cooling bath was dissolved (4S,5R)-4-(Phenylmethoxy)-5-[(phenylmethoxy)methyl]-1-cyclopentene-1-carboxylic acid methyl ester 7 (3.62 g, 10.2 mmol) in DCM (40 mL). The solution was cooled to −78° C. and diisobutylaluminum hydride (1 M in toluene, 22.4 mL, 22.4 mmol) was added into the solution over the course of 10 minutes. After stirring at −78° C. for 1 hour the reaction mixture was quenched with a saturated solution of potassium sodium tartrate (Rochelle salt, 50 mL) and stirred at room temperature overnight. The organic layer was diluted with ethyl acetate, separated, dried (sodium sulfate) and concentrated in vacuo to afford the crude allylic alcohol as colorless oil (3.06 g, 90%). After standing at room temperature the title compound crystallized out as a white solid.

Workup

customTo a round bottomed flask equipped with an argon inlet, magnetic stirrer
temperaturecooling bath
customwas quenched with a saturated solution of potassium sodium tartrate (Rochelle salt, 50 mL)
stirringstirred at room temperature overnight
additionThe organic layer was diluted with ethyl acetate
customseparated
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3e6a7fec2296476eaab871341dd49234
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550619B2

Reaction notes

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