Isobutyraldehyde → HCID 14692987, compound

HRID 1608070Notes

Reaction equation

HRID 1608070 reaction equation
[Cl-].C[Al+]C.[CH3:5]CCCCC.[CH3:11][C:12]1[CH2:17][C:16]([CH3:19])([CH3:18])[CH:15]([CH2:20][C:21]2S(=C)C=CC=2)[C:14]([CH3:28])([CH3:27])[CH:13]=1.[CH:29](=[O:33])[CH:30]([CH3:32])[CH3:31]>ClCCl>[CH3:31][CH:30]([CH:29]([OH:33])[CH2:5][C:20](=[CH2:21])[CH:15]1[C:16]([CH3:18])([CH3:19])[CH2:17][C:12]([CH3:11])=[CH:13][C:14]1([CH3:27])[CH3:28])[CH3:32]

Participants

6

Reactant 4

HCID 6561IsobutyraldehydeHCID 8058HexaneHCID 16686359Dimethylalumanylium chlorideHCID 86743399HCID 86743399, compound

Product 1

HCID 14692987HCID 14692987, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylaluminum chloride (3 mL of a 1M hexane solution) was reacted with a solution of 1,3,3,5,5-pentamethyl-4-(1-methylenethenyl)-1-cyclohexene (0.48 g, 0.0025 mol) and isobutyraldehyde (0.18 g, 0.0025 mol) in dichloromethane (10 mL) according to the procedure described in Example 3. Work-up and chromatography gave 0.300 g (45% yield) of α-(1-methylethyl)-2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol, bp (kugelrohr bath) 135° C., 0.5 mm (GLC purity 94.4%, 2:1 mixture of diastereomers). 1H-NMR (60 MHz, CDCl3) δ0.88-1.07 (18H, 1d and 1 broad s), 1.4-2.4 (10H, m), 3.2-3.7 (1H, m) 4.9-5.2 (3H, m); IR (film) vmax 3450, 2950, 1640, 1465, 1380, 1360 cm-1 ; MS m/e 264, 249, 246, 221, 203, 177, 107, 96. The mass spectra of the diastereomers were nearly identical.

Workup

  1. customchromatography gave

Sources & evidence

ORD record
ord-1d34d6bf1bb44ea49114a432434f21cc
Source dataset
uspto-grants-1989_09
Patent number
US04868339

Reaction notes

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