4-Toluenesulfonyl chloride → HCID 53971946, compound

HRID 2052414Notes

Reaction equation

HRID 2052414 reaction equation
COC(=O)CC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(C[C@@H](OCOCCOC)CC2)=CC3)CC1)C.COCCO[AlH2-]OCCOC.[Na+].O1CCCCC1OC1CCCCO1.[CH3:60][O:61][CH2:62][CH2:63][O:64][CH2:65][O:66][C@H:67]1[CH2:89][CH2:88][C@@:87]2([CH3:90])[C:69](=[CH:70][CH2:71][C@@H:72]3[C@@H:86]2[CH2:85][CH2:84][C@@:83]2([CH3:91])[C@H:73]3[CH2:74][CH2:75][C@@H:76]2[C@H:77]([CH3:82])[CH2:78][CH2:79][CH2:80][OH:81])[CH2:68]1.[S:92](Cl)([C:95]1[CH:101]=[CH:100][C:98]([CH3:99])=[CH:97][CH:96]=1)(=[O:94])=[O:93]>N1C=CC=CC=1>[CH3:60][O:61][CH2:62][CH2:63][O:64][CH2:65][O:66][C@H:67]1[CH2:89][CH2:88][C@@:87]2([CH3:90])[C:69](=[CH:70][CH2:71][C@@H:72]3[C@@H:86]2[CH2:85][CH2:84][C@@:83]2([CH3:91])[C@H:73]3[CH2:74][CH2:75][C@@H:76]2[C@H:77]([CH3:82])[CH2:78][CH2:79][CH2:80][O:81][S:92]([C:95]2[CH:101]=[CH:100][C:98]([CH3:99])=[CH:97][CH:96]=2)(=[O:94])=[O:93])[CH2:68]1

Participants

7

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 263182Tetrahydropyranyl etherHCID 16684438Red-AlHCID 22809232HCID 22809232, compoundHCID 53903360HCID 53903360, compound

Product 1

HCID 53971946HCID 53971946, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 3β-(methoxyethoxymethoxy)-5-cholenic acid methyl ester was reduced with Vitride as described for the tetrahydropyranyl ether in Example 3. The resulting compound, the 3β-(methoxyethoxymethoxy)-24-hydroxy-5-cholene, was treated with tosyl chloride in pyridine and the 3β-(methoxyethoxymethoxy)-24-tosyloxy-5-cholene obtained. The tosyloxy compound was heated in dimethylformamide with potassium cyanide, and the tosyloxy group exchanged for the cyano group. 2.1 mmole of the 3β-(methoxyethoxymethoxy)-25-cyano-5-cholene was stirred with 2.36 g (10.5 mmole) of zinc bromide in 15 ml of methylene chloride. The insoluble material was removed by filtration, washed with ether, and the combined filtrates extracted with saturated aqueous solutions of sodium bicarbonate and sodium chloride. After drying, the solvents were evaporated, and the residue sponified with alkali. The 3β-hydroxy-5-homocholenic acid was obtained from the acidified saponification mixture.

Sources & evidence

ORD record
ord-0862e9a80253419fb22fd057206923cd
Source dataset
uspto-grants-1980_01
Patent number
US04183852

Reaction notes

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