(6Z,9Z)-18-bromooctadeca-6,9-diene → HCID 86678086, compound

HRID 2274710Notes

Reaction equation

HRID 2274710 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Si:20]([O:27][CH:28]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]/[CH:39]=[CH:40]\[CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:29][CH:30]=[O:31])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C1COCC1>[Si:20]([O:27][CH:28]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]/[CH:39]=[CH:40]\[CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:29][CH:30]([OH:31])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 10065142(6Z,9Z)-18-bromooctadeca-6,9-dieneHCID 86678085HCID 86678085, compound

Product 1

HCID 86678086HCID 86678086, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
45 °C

Procedure

A suspension of Mg (165 mg, 6.77 mmol) in THF (1 mL) was treated with a solution of linoleyl bromide (2.03 g, 6.15 mmol) in THF (1.5 mL) in one portion. The suspension was heated (45° C.) and stirred (4 h). The newly generated Grignard was then treated with a solution of (11Z,14Z)-3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienal (5) (2.0 g, 4.73 mmol) in THF (8 mL) and stirred (2 h). The reaction mixture was quenched by the addition of H2O, extracted with ether, washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was subjected to chromatography (2%→3% EtOAc-hexanes) to yield (6Z,9Z,29Z,32Z)-21-((tert-butyldimethylsilyl)oxy)octatriaconta-6,9,29,32-tetraen-19-ol (6)(2.44 g, 77%) as a pale yellow oil. Rf 0.59 (10% EtOAc-hexanes), FW 673.22, C44H84O2Si.

Workup

  1. stirringstirred (2 h)
  2. customThe reaction mixture was quenched by the addition of H2O
  3. extractionextracted with ether
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7ced40d9afc546a89bc3ad72063ee196
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

Loading…