Ethyl Acetate → HCID 14539526, compound

HRID 330629Notes

Reaction equation

HRID 330629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)[CH2:10]Cl)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CC[O:33]C(C)=O>C1COCC1.OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)[CH2:10][OH:33])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 19986228HCID 19986228, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14539526HCID 14539526, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

The acyl chloride prepared in Step A was dissolved into 150 mL of tetrahydrofuran and was chilled to -78° C. under argon. To this pale brownish solution at -78° C. was added 8.0 mL lithium aluminum hydride in THF solutions (1.0 Molar). Analytical TLC after 15 minutes showed only one mobile spot at Rf =0.23 (50% EtOAc in hexanes v/v). The crude reaction mixture was diluted with 2M H2SO4 (20 ml). The aqueous layer was extracted with ethyl acetate (40 mL×2). Organic layers were combined, dried over MgSO4 and concentated under reduced pressure to give 3.64 g (100%) of the title compound. The crude allylic alcohol was used immediaely in the next step without further purification. MS (CI): m/e=328 for (M+H)+ ;

Workup

  1. customThe crude reaction mixture
  2. extractionThe aqueous layer was extracted with ethyl acetate (40 mL×2)
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-6bed77930c854930b1a449951cc8b284
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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