Heptane → HCID 53628374, compound

HRID 1024948Notes

Reaction equation

HRID 1024948 reaction equation
[Si:1]([O:18][C@H:19]([CH3:23])[C:20]([OH:22])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CCCCCCC.[C:43]([O:49][CH2:50][CH3:51])(=[O:48])[CH2:44]C(O)=O>C1COCC1>[Si:1]([O:18][C@H:19]([CH3:23])[C:20](=[O:22])[CH2:44][C:43]([O:49][CH2:50][CH3:51])=[O:48])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 682631,1'-CarbonyldiimidazoleHCID 70615Monoethyl malonateHCID 15286443HCID 15286443, compound2×

Product 1

HCID 53628374HCID 53628374, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2R)-2-{[tert-Butyl(diphenyl)silyl]oxy}propanoic acid (the product from step i, 7.85 g) in THF (300 ml) was added CDI (4.26 g) and the reaction was stirred at room temperature for approximately 15 mins. In a separate flask (71.7 ml) of a 1M heptane solution was added to a solution of ethyl hydrogen malonate (9.47 g) in THF (300 ml) at 0° C. This solution was then allowed to warm to RT. The acyl imidazole solution was then transferred to the flask which contained the magnesium salt and the reaction was monitored for the next 2 d. When the reaction was complete it was quenched by the addition of 250 ml of sat. aq NH4Cl solution. The reaction mixture was then extracted with Et2O (3×200 ml). The combined organics were dried (MgSO4), filtered and reduced to yield a clear oil which was purified by column chromatography on silica gel 4% EtOAc/96% iso-hexane. This gave the subtitle compound as a colourless oil. Yield: 2.0 g

Workup

  1. temperatureto warm to RT
  2. customwas monitored for the next 2 d
  3. customwas quenched by the addition of 250 ml of sat. aq NH4Cl solution
  4. extractionThe reaction mixture was then extracted with Et2O (3×200 ml)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customto yield a clear oil which
  8. customwas purified by column chromatography on silica gel 4% EtOAc/96% iso-hexane

Sources & evidence

ORD record
ord-aff865115395424c9f9f324f0768fb91
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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