Diethyl Ether → HCID 69050013, compound

HRID 1821546Notes

Reaction equation

HRID 1821546 reaction equation
C[Mg]Cl.[CH2:4]([O:11][C@@H:12]([CH3:33])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]([OH:32])[CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+].[CH2:36](OCC)C>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH2:4]([O:11][C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]([OH:32])[CH2:20][CH3:36])[CH3:33])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 86612733HCID 86612733, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 69050013HCID 69050013, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To 11.8 ml of a commercially available solution of 20% methyl magnesium chloride (31.4 mmol) in tetrahydrofuran were added 20 ml abs. tetrahydrofuran. The solution was cooled to −78° C., and 595 mg (3.14 mmol) copper-I-iodide were added. After stirring for 15 min, a solution of 4.55 g (10.5 mmol) (2R,9S)-9-benzyloxy-1(p-tolylsulfonyloxy)-decane-2-ol in 10 ml abs. tetrahydrofuran was added over a period of 2 h. The solution was warmed to −30° C. and stirred for another hour. Subsequently, 150 ml saturated aqueous ammonium chloride and 50 ml diethyl ether were added at 0° C. The aqueous layer was extracted three times with 150 ml ethyl acetate. The combined organic layers were dried over magnesium sulphate and concentrated in vacuo. Flash chromatography (16% ethyl acetate in hexane) furnished 2.6 g (9.4 mmol, 90%) (2S,9S)-2-benzyloxyundecane-9-ol

Workup

  1. temperatureThe solution was warmed to −30° C.
  2. stirringstirred for another hour
  3. extractionThe aqueous layer was extracted three times with 150 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f79c6bda9dd646f6b481d4345808f0b5
Source dataset
uspto-grants-2009_10
Patent number
US07608254B2

Reaction notes

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