Diethyl Ether → HCID 23325911, compound

HRID 1380714Notes

Reaction equation

HRID 1380714 reaction equation
[Li].C[CH:3]1[CH2:9][CH2:8][CH:7]2[C:10](=[O:11])[C:4]1([CH3:12])[CH2:5][CH2:6]2.[CH:13](Br)([CH3:15])[CH3:14].[CH3:17]COCC>>[CH3:17][C:7]12[C:10]([CH:13]([CH3:15])[CH3:14])([OH:11])[C:4]([CH3:12])([CH2:5][CH2:6]1)[CH2:3][CH2:9][CH2:8]2

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 63582-BromopropaneHCID 3028194LithiumHCID 23325915HCID 23325915, compound

Product 1

HCID 23325911HCID 23325911, compound

Conditions

Temperature
40 °C

Procedure

10,5 g (1,5 mole) lithium (finelly divided) and 76 g (0,5 mole) dimethylbicyclo[3.2.1]octane-8-one (4) were added to 800 ml ether (absolute). Into this mixture a solution of 92,3 g (9,75 mole) isopropylbromide in 300 ml absolute ether was dropwise added at -10° C. within 4 h. After 1 h of stirring at 40° C. the mixture was hydrolysed and processed for isolation in usual manner. By distillation over a turning band column 46 g (47%) of 10 having a boiling point (1 mm) of 76° C. resulted from the raw product. IR: 3500/3600 cm-1 (O--H).--NMR (CCl4): δ=0,91, s (1-, 5-CH3), 1,15, d, J=7 Hz (CH3 --CH--CH3), 1,55 ppm, br. s (6-, 7-CH2).C13H24O (M=196,32)

Workup

  1. distillationBy distillation over a turning band column 46 g (47%) of 10 having a boiling point (1 mm) of 76° C.

Sources & evidence

ORD record
ord-e23f681cec464c2cbf2c2452040146d7
Source dataset
uspto-grants-1986_04
Patent number
US04582945

Reaction notes

Loading…