HCID 15023219, compound → HCID 14890667, compound

HRID 1651315Notes

Reaction equation

HRID 1651315 reaction equation
[C:1]([C:3](=[C:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:4](Cl)=[O:5])#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.OS(O)(=O)=O>[C:1]([C:3](=[C:7]([C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:4][OH:5])#[N:2]

Participants

5

Reactant 2

HCID 15023219HCID 15023219, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14890667HCID 14890667, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

The acyl chloride prepared in Step A was dissolved in 40 mL of tetrahydrofuran and was chilled to -78° C. under an inert atmosphere. To this pale greenish solution at -78° C. was added 10 mL lithium aluminum hydride in tetrahydrofuran solution (1M, 10 mmol). Reduction was allowed to proceed at -78° C. for 20 minutes before it was diluted with H2SO4 dilute solution (2M, 20 mL). The desired product was extracted twice into ethyl acetate (40 mL×2). Organic layers were combined, dried over MgSO4 and concentrated under reduced pressure to give 2.64 g (69.4%) of the title compound. The crude allylic alcohol was used in the next step without further purification. An analytically pure sample was prepared by crystallization from a mixture of ethyl acetate-hexanes (1:9, v/v) m.p.=110°-112° C.

Workup

  1. extractionThe desired product was extracted twice into ethyl acetate (40 mL×2)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0719751f45c4fb4ba78893f41e76d2d
Source dataset
uspto-grants-1990_05
Patent number
US04927944

Reaction notes

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