Hydrochloric Acid → HCID 86678085, compound

HRID 2274709Notes

Reaction equation

HRID 2274709 reaction equation
[Si:1]([O:8][CH:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:10][C:11](OC)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.Cl>C(Cl)Cl>[Si:1]([O:8][CH:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:10][CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 86678084HCID 86678084, compound

Product 1

HCID 86678085HCID 86678085, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (11Z,14Z)-methyl 3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienoate (4) (5.0 g, 11.0 mmol) in CH2Cl2 (75 mL) was cooled (−78° C.) and treated, dropwise, with DIBAL (11.0 mL, 11.0 mmol; as a 1M solution in hexanes). The mixture was then warmed (−20° C.-−30° C.) and stirred (60 min). The mixture was poured into cold HCl (5% aq.), extracted with CH2Cl2, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was subjected to chromatography (1%→10% EtOAc-hexanes) to yield (11Z,14Z)-3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienal (5) (3.7 g, 79%) as a pale yellow oil. Rf 0.64 (10% EtOAc-hexanes), FW 422.79, C26H50O2Si.

Workup

  1. additiontreated
  2. temperatureThe mixture was then warmed (−20° C.-−30° C.)
  3. extractionextracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6fb6c2cec27d4e44b456f68f7abf002c
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

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