Diethyl Ether → HCID 70231346, compound

HRID 379633Notes

Reaction equation

HRID 379633 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH:21]=[O:22].C[Li].[CH3:25]COCC>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH:21]([OH:22])[CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 88223057HCID 88223057, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 70231346HCID 70231346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of aldehyde from Example 9, Step 2 (1.5 g, 4.8 mmol) in THF (25 mL) at 0° C. there was added methyl lithium (1.4 M) in ether (3.8 mL, 5.3 mmol) and the mixture stirred at 0° C. for 45 minutes; it was then quenched with saturated aqueous ammonium chloride and extracted with ether to afford crude material which was chromatographed on silica gel to provide the title compound as a reddish syrup.

Workup

  1. customit was then quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ether
  3. customto afford crude material which
  4. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-3670f07fc28a48838705c8f281546851
Source dataset
uspto-grants-2001_10
Patent number
US06300346B1

Reaction notes

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