Hydrochloric Acid → HCID 59913818, compound

HRID 989614Notes

Reaction equation

HRID 989614 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH2:18][CH2:17][C:16](=[O:23])[CH2:15][C:14]=1[CH2:13][CH:12]=3)(=[O:3])[CH3:2].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].Cl>C1COCC1>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH2:18][CH2:17][CH:16]([OH:23])[CH2:15][C:14]=1[CH2:13][CH:12]=3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 16684435Lithium tritertbutoxyaluminohydrideHCID 57009121HCID 57009121, compound

Product 1

HCID 59913818HCID 59913818, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ketone 9 (1.03 g, 3.28 mmol) in dry THF (20 mL) at 0° C. under nitrogen was treated, via syringe, with lithium tri-tert-butoxyaluminohydride (1.0 M, 1.5 eq, 4.92 mL, 4.92 mmol). After 2 h the solution was poured into 1N HCl (100 mL). The layers were separated and the aqueous layer was extracted with ether (3×50 mL). The organic layers were combined, washed with saturated aqueous NaCl solution (50 mL), dried over magnesium sulfate and concentrated under reduced pressure to give a white solid (1.08 g), Rf0.3 (30% EtOAc/hexane), which was used without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ether (3×50 mL)
  3. washwashed with saturated aqueous NaCl solution (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2a7ec9a8d69463e97c99db989eceb52
Source dataset
uspto-grants-2002_10
Patent number
US06458778B1

Reaction notes

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