Acetic Anhydride → HCID 131717831, compound

HRID 1614406Notes

Reaction equation

C(OC(=O)C)(=O)C.[OH:8][CH:9](CCCCCCCC)/[CH:10]=[CH:11]/[CH:12]=[CH:13]/C1C=CC=CC=1CCCCCO.[C:34]1([Si:40]([O:51][Si:52]([C:65]([CH3:68])([CH3:67])[CH3:66])([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:41]([CH3:44])([CH3:43])[CH3:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>N1C=CC=CC=1>[CH2:9]([OH:8])[CH2:10][CH2:11][CH2:12][CH3:13].[C:59]1([Si:52]([O:51][Si:40]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:65]([CH3:68])([CH3:67])[CH3:66])[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1

Participants

Conditions

Temperature: 25 °C

Procedure

For acetylation, 0.5 ml of acetic anhydride is added to a solution of 310 mg of the above-described alcohol in 2 ml of pyridine and stirred for 16 hours at 25° C. Then, it is concentrated by evaporation with adding toluene in a vacuum and the residue is chromatographed on silica gel. With hexane/1-5% of methyl-tert-butyl ether, 265 mg of 5-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-phenyl]-pentan-1-ol-diphenyl-tert-butylsilyl ether is obtained as a colorless oil.

Workup

concentrationThen, it is concentrated by evaporation with adding toluene in a vacuum
customthe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-e72e7b95caa44ca09c1ae260594782c8
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196570

Reaction notes

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