Hexane → HCID 54509049, compound

HRID 1614728Notes

Reaction equation

HRID 1614728 reaction equation
O.[OH-].[Li+].[O:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[O:10][CH2:11][C:12]#[C:13][CH:14]=[CH:15][C:16]#[C:17][Si](C)(C)C.CCCCCC>O1CCCC1.O.CCOCC>[O:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[O:10][CH2:11][C:12]#[C:13][CH:14]=[CH:15][C:16]#[CH:17]

Participants

7

Reactant 3

HCID 8058HexaneHCID 168937Lithium hydroxide, monohydrateHCID 54246246HCID 54246246, compound

Product 1

HCID 54509049HCID 54509049, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (22.55 g, 0.54 mol) was added in one portion to a solution of 21.62 g (82.38 mmol) silyl diynene (compound N of step (b)) in 240 mL tetrahydrofuran and 40 mL water stirring at 25° C. The reaction was stirred for 1.58 h and then diluted with 1:1 ether:hexane and water. The aqueous layer was reextracted with three portions of ether and then the combined organic extracts were dried over anhydrous sodium sulfate. Flash chromatography over silica gel using a gradient of 2.5 to 10% ethyl acetate/hexane as eluent provided 15.69g (98%) of brown liquid:

Workup

  1. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-1fee4fe9e6b24269bb507774ed5e9da3
Source dataset
uspto-grants-1993_03
Patent number
US05198560

Reaction notes

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