(4S)-4-(2-tetrahydropyranyloxy)-2-nonynal → (4S)-4-(2-tetrahydropyranyloxy)nonanal

HRID 973340Notes

Reaction equation

HRID 973340 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:9]#[C:10][CH:11]=[O:12]>O1CCOCC1.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH:11]=[O:12]

Participants

4

Reactant 1

HCID 86735172(4S)-4-(2-tetrahydropyranyloxy)-2-nonynal

Product 1

HCID 86735173(4S)-4-(2-tetrahydropyranyloxy)nonanal

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4S)-4-(2-Tetrahydropyranyloxy)-2-nonynal (54.6 g., 0.23 mole) in dioxane (200 ml.) is hydrogenated at room temperature and a pressure of 2-3 atmospheres over a 5% palladium on charcoal catalyst to yield (4S)-4-(2-tetrahydropyranyloxy)nonanal purified by distillation at reduced pressure.

Workup

  1. customis hydrogenated at room temperature

Sources & evidence

ORD record
ord-18ee139a8b1e418b8dc8b77af084e174
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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