Hydrochloric Acid → 6-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridine-2-carbaldehyde

HRID 977598Notes

Reaction equation

HRID 977598 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](/[CH:13]=[CH:14]/[CH:15]([O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[N:8]=1.CN(C)[CH:44]=[O:45].Cl>C(OCC)C.O1CCCC1>[Si:25]([O:24][CH:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])/[CH:14]=[CH:13]/[C:9]1[N:8]=[C:7]([CH:44]=[O:45])[CH:12]=[CH:11][CH:10]=1)([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 883633822-bromo-6-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridineHCID 178418339Butyllithium

Product 1

HCID 883633866-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridine-2-carbaldehydeYield 84.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

1.16 ml of n-butyllithium (1.6 molar in hexane) is instilled in a suspension of 500 mg of 2-bromo-6-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridine in 2 ml of diethyl ether and 1 ml of tetrahydrofuran at -80° C. under argon atmosphere. After completion of the addition, the reaction mixture is stirred for 15 minutes at -40° C., cooled to -80° C. and mixed by instillation at this temperature with 140 mg of dimethylformamide. After 4 hours at -80° C., the reaction mixture is hydrolyzed with 3 ml of 2 n hydrochloric acid, the organic phase is separated, dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-10% ethyl acetate. 385 mg of 6-[(1E)-(3RS)-3-tert- butyldiphenylsilyloxy-1-undecenyl]-pyridine-2-carbaldehyde is obtained as yellow oil.

Workup

  1. additionAfter completion of the addition
  2. temperaturecooled to -80° C.
  3. waitAfter 4 hours at -80° C.
  4. customthe organic phase is separated
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customthe residue is chromatographed on silica gel with hexane/0-10% ethyl acetate

Sources & evidence

ORD record
ord-50f24eab820949dbb9d937f78a2c2f48
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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