Hydrochloric Acid → HCID 70231801, compound

HRID 2371493Notes

Reaction equation

HRID 2371493 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)/[C:3]=1[CH2:20][C:21](OC)=[O:22].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.Cl>C1COCC1>[OH:22][CH2:21][CH2:20][C:3]1/[C:4](=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)/[C:5]2[C:10]([C:2]=1[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 86745528HCID 86745528, compound

Product 1

HCID 70231801HCID 70231801, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester from Step 3 (270 mg, 0.83 mmol) in dry THF (5 mL) at 0° C. was added a solution of diisobutyl aluminum hydride (1M) in toluene (2.1 mL, 2.1 mmol, 3.5 eq). After 1 hour, the reaction mixture was added dropwise to a solution of 1N aqueous HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and evaporated to dryness. The crude product was chromatographed on silica gel eluting with a 1:3 mixture of ethyl acetate-hexane to afford pure title compound as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe crude product was chromatographed on silica gel eluting with a 1:3 mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-65ac5e5aee994d9c829bd0af53ab0e23
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Reaction notes

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