Magnesium → 1-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-

HRID 1659822Notes

Reaction equation

HRID 1659822 reaction equation
[Mg].BrCC[C@H](C)CCCC(C)C.BrC[C@@H](C)CCOC1CCCCO1.[CH3:26][C@H:27]([CH2:37][CH2:38][CH2:39][C@H:40]([CH3:47])[CH2:41][CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:28][CH2:29][O:30]C1CCCCO1>O1CCCC1>[CH3:26][C@H:27]([CH2:37][CH2:38][CH2:39][C@H:40]([CH3:47])[CH2:41][CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:28][CH2:29][OH:30]

Participants

6

Reactant 4

HCID 5462224MagnesiumHCID 12801557(R)-1-bromo-3,7-dimethyloctaneHCID 13937367HCID 13937367, compoundHCID 22806778tetrahydro-2-{[(3R,7R)-3,7,11-trimethyldodecyl]-oxy}-2H-pyran

Product 1

HCID 1590641-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard solution is prepared in the manner described above in Example 10 from 0.3 g (12.4 mmol) of magnesium and 2.54 g (11.5 mmol) of (R)-1-bromo-3,7-dimethyloctane in 10 ml of absolute tetrahydrofuran. To this solution are added dropwise at 0° 1.45 g (5.57 mmol) of 2-[(S)-4-bromo-3-methylbutoxy]-tetrahydro-2H-pyran followed by 0.3 ml of a 0.1 molar solution of Li2CuCl4 in tetrahydrofuran. This reaction mixture is stirred at 0° for 3 hours. The working-up as well as the hydrolysis of the tetrahydro-2-{[(3R,7R)-3,7,11-trimethyldodecyl]-oxy}-2-H-pyran obtained to (3R,7R)-3,7,11-trimethyl-1-dodecanol is effected in the manner described above in Example 10. The yield of (3R,7R)-3,7,11-trimethyl-1-dodecanol amounts, after bulb-tube distillation at 90°-95°/0.05 Torr, to 0.5 g (43% based on 2-[ (S)-4-bromo-3-methylbutoxy]-tetrahydro-2H-pyran); [α]D20 =+3.9° (c=1.05, n-octane).

Workup

  1. customA Grignard solution is prepared in the manner

Sources & evidence

ORD record
ord-7613ec00440246f3b029128908c68078
Source dataset
uspto-grants-1981_12
Patent number
US04305876

Reaction notes

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