Diisopropylamine → HCID 86678091, compound

HRID 2274714Notes

Reaction equation

HRID 2274714 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH2:13]([CH:31]([C:50]([CH:52]([CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78]/[CH:79]=[CH:80]\[CH2:81]/[CH:82]=[CH:83]\[CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]/[CH:61]=[CH:62]\[CH2:63]/[CH:64]=[CH:65]\[CH2:66][CH2:67][CH2:68][CH2:69]C)=[O:51])CCCCCCCC/C=C\C/C=C\CCCCC)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29]C.[Li].C1C[O:93]CC1>>[CH2:53]([CH:52]([CH:71]([OH:93])[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78]/[CH:79]=[CH:80]\[CH2:81]/[CH:82]=[CH:83]\[CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[C:50](=[O:51])[CH2:31][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59]/[CH:60]=[CH:61]\[CH2:62]/[CH:63]=[CH:64]\[CH2:65][CH2:66][CH2:67][CH2:68][CH3:69]

Participants

6

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 3028194LithiumHCID 89428302HCID 89428302, compoundHCID 178418339Butyllithium

Product 1

HCID 86678091HCID 86678091, compoundYield 62%

Conditions

Temperature
-78 °C

Procedure

To a cooled (−40° C.) solution of N,N,-di-isopropylamine (462 μL, 3.27 mmol) in THF (9 mL) was added nBuLi (1.45 mL, 3.63 mmol as a 2.5M solution in hexanes). After stirring (40 min) the solution was cooled (−78° C.) and treated with di-linoleylmethylketone (1.50 g, 2.85 mmol, neat) dropwise. After stirring (40 min) the newly generated lithium enoloate was added to a cold (−78° C.) solution of linoleyl aldehyde (804 mg, 3.04 mmol) in THF (4 mL). After stirring (1 h, −78° C.) the mixture was quenched by the addition of sat. aq. NH4Cl, then extracted with EtOAc, dried (Na2SO4), filtered and concentrated. The crude material was subjected to chromatography (0.5%→1% EtOAc-hexanes) to yield (6Z,9Z,29Z,32Z)-20-((8Z,11Z)-heptadeca-8,11-dien-1-yl)-21-hydroxyoctatriaconta-6,9,29,32-tetraen-19-one (10) (1.50 g, 62%) as a colorless oil. Rf 0.27 (5% EtOAc-hexanes), FW 791.39, C55H98O2.

Workup

  1. stirringAfter stirring (1 h, −78° C.) the mixture
  2. customwas quenched by the addition of sat. aq. NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6183f9abde364f459976c199839897d8
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

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