Pivalaldehyde → HCID 71767061, compound

HRID 1771414Notes

Reaction equation

HRID 1771414 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][C:7]2([C:13]1[NH:14][CH2:15][CH2:16][N:17]=1)[CH3:12].C([Li])(C)(C)C.[CH3:23][C:24]([CH3:28])([CH3:27])[CH:25]=[O:26]>C1COCC1.CCCCC>[NH:14]1[CH2:15][CH2:16][N:17]=[C:13]1[C:7]1([CH3:12])[C:8]2[C:3](=[C:2]([CH:25]([OH:26])[C:24]([CH3:28])([CH3:27])[CH3:23])[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][O:6]1

Participants

6

Reactant 3

HCID 12417PivalaldehydeHCID 89853002HCID 89853002, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 71767061HCID 71767061, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(5-bromo-1-methylisochroman-1-yl)-4,5-dihydro-1H-imidazole (Example 2, 0.075 g) in 2 ml of THF was added 0.33 ml of tert-butyl lithium solution in pentane (1.7M) at −78° C. followed by addition of 1.2 ml of 20.8M solution of trimethylacetaldehyde in THF. After stirring at −78° C. for 15 min, the reaction was quenched with ice. The title compound was isolated with separation methods A and G. (Yield 0.003 g).

Workup

  1. customthe reaction was quenched with ice

Sources & evidence

ORD record
ord-ceef52b4538649b8a22bfda4e362c553
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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