Hydrochloric Acid → HCID 10261083, compound

HRID 2227112Notes

Reaction equation

S(OC1CCC(C)=CC1)([C:4]1[CH:10]=C[C:7](C)=[CH:6][CH:5]=1)(=O)=O.Cl.O1[CH2:24][CH2:23][CH2:22][CH2:21]1>[Cl-].[Zn+2].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:21][C:22]1[CH2:7][CH2:6][CH:5]([C:4]#[CH:10])[CH2:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of lithium acetylide ethylenediamine complex (4.53 g) in dry tetrahydrofuran (38 mL), stirred and cooled to 0° C., is slowly added a 0.5M solution of zinc chloride in dry tetrahydrofuran (100 mL). The mixture is stirred at 10° C. for 30 minutes, then cooled to 0° C. again. A solution of tosylate 4D (R=methyl) (5 g) in dry tetrahydrofuran (11 mL) is then added dropwise, followed by addition of palladium tetrakis(triphenylphosphine) (650 mg). The reaction mixture is stirred overnight at room temperature. The mixture is poured into 10% HCl and extracted into ether. The combined organic layers are sequentially washed with a dilute sodium carbonate solution and brine, then dried over magnesium sulfate. The solvent is removed in vacuo.

Workup

temperaturecooled to 0° C. again
stirringThe reaction mixture is stirred overnight at room temperature
extractionextracted into ether
washThe combined organic layers are sequentially washed with a dilute sodium carbonate solution and brine
dry with materialdried over magnesium sulfate
customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-76188eff5de44005a6eb7ac3a8597646
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06413448B1

Reaction notes

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