Diisobutylaluminumhydride → HCID 86636788, compound

HRID 511997Notes

Reaction equation

HRID 511997 reaction equation
O(CCCCCCC=O)C1C=CC=CC=1.C([O:18][C:19](=O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:29][CH:28]=1)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:34]([O:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=[O:18])=[CH:32][CH:31]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 21225700DiisobutylaluminumhydrideHCID 66930919HCID 66930919, compoundHCID 86636787HCID 86636787, compound

Product 1

HCID 86636788HCID 86636788, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-[4-(Benzyloxy)phenoxy]heptanal 62.2 was synthesized analogous to the preparation of 62.1 using 61.2/20.4 (0.624 g, 2 mmol) and diisobutylaluminum hydride (4.5 mL, 4.5 mmol, using a 1M solution in hexanes) in THF (20 mL). Purification by flash column chromatography on silica gel gave 62.2 (0.39 g, 63% yield) as a white solid (m p 65-67° C.).

Workup

  1. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f5dfe08517454e2b88b5d44e5d2fac3b
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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