Dimethyl Sulfoxide → HCID 131711716, compound

HRID 127558Notes

Reaction equation

HRID 127558 reaction equation
[O:1]([CH2:19][CH:20]([CH3:48])[CH2:21][CH2:22][CH2:23][C:24]([CH3:47])([OH:46])[C:25](=[O:45])[CH2:26][CH2:27][C:28]1([O:44][CH2:43][CH2:42][O:41]1)[CH2:29][O:30][S:31]([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OC(=O)C)(=O)C.[CH3:56][S:57]([CH3:59])=O>>[O:1]([CH2:19][CH:20]([CH3:48])[CH2:21][CH2:22][CH2:23][C:24]([CH3:47])([O:46][CH2:56][S:57][CH3:59])[C:25](=[O:45])[CH2:26][CH2:27][C:28]1([O:41][CH2:42][CH2:43][O:44]1)[CH2:29][O:30][S:31]([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 131711717HCID 131711717, compound

Product 1

HCID 131711716HCID 131711716, compoundYield 91%

Procedure

11-t-Butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-6-hydroxy-5-oxo-1-tosyloxyundecane (1.15 g) is dissolved in dimethyl sulfoxide (8.15 ml), acetic anhydride (8.15 ml) is added and the resulting solution is stirred for 20 hours. The solvents are removed in vacuo below 70° C. and the residue is partitioned between ether and saturated sodium bicarbonate solution. The organic layer is washed with brine and dried (sodium sulfate). The solvent is removed in vacuo to give 11-t-butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-6-methylthiomethoxy-5-oxo-1-tosyloxyundecane (1.13 g, 91%) as a yellow oil; nmr (CDCl3,δ) 0.88 (d, CH3CH), 1.04 [s, (CH3)3 -C], ##STR29## 2.17 (s, SCH3), 2.42 (s, CH3 -Ph), 3.42 (d, OCH2CH), 3.89 (s, OCH2CH2O and TsOCH2C), 4.41 (s, OCH2S), 7.2-7.9 (aromatic H).

Workup

  1. customThe solvents are removed in vacuo below 70° C.
  2. customthe residue is partitioned between ether and saturated sodium bicarbonate solution
  3. washThe organic layer is washed with brine
  4. dry with materialdried (sodium sulfate)
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ab6d5c48890c4c0d80a601b00d6ea5d8
Source dataset
uspto-grants-1981_03
Patent number
US04256644

Reaction notes

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