Hydrochloric Acid → 5-Triphenylmethoxy-1-octyne

HRID 461273Notes

Reaction equation

HRID 461273 reaction equation
Cl[CH2:2][CH2:3][CH:4]([O:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][CH2:6][CH3:7].CS(C)=O.O.Cl.[CH3:34][CH2:35]OCC>>[C:10]1([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][CH:4]([CH2:5][CH2:6][CH3:7])[CH2:3][CH2:2][C:34]#[CH:35])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 3283Diethyl EtherHCID 203810131-Chloro-3-triphenylmethoxyhexane

Product 1

HCID 203810475-Triphenylmethoxy-1-octyne

Procedure

To a stirred solution of 32.2 g. (85 mmoles) of 1-chloro-3-triphenylmethoxyhexane (Example 750a) in 25 ml. of dimethylsulfoxide (DMSO) is added a solution of 9.4 g. (102 mmoles) of lithium acetylide-ethylene diamine complex in 60 ml. of DMSO during 10 minutes while maintaining a temperature of 25°-30° C. After 3.5 hours the mixture is diluted with ether and treated successively with water and 4N hydrochloric acid while cooling in an ice bath. The phases are separated, and the aqueous phase is extracted with ether-petroleum ether. The combined extracts are washed successively with water and saturated sodium chloride solution dried over magnesium sulfate, and concentrated. The product is then purified by column chromatography of the residue on Florisil.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ether-petroleum ether
  4. washThe combined extracts are washed successively with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe product is then purified by column chromatography of the residue on Florisil

Sources & evidence

ORD record
ord-502642c3bc62450d9df1f477a851a94a
Source dataset
uspto-grants-1977_12
Patent number
US04061672

Reaction notes

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