3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]Benzaldehyde → 3-(6-Chloro-1,3-benzthiazin-2-yl-transethenyl)benzyl alcohol t-butyldimethylsilyl ether

HRID 1109781Notes

Reaction equation

HRID 1109781 reaction equation
[CH3:1][CH:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:4]=2[S:3]1.[Si:13]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=O)[CH:23]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>N1CCCCC1.C1C=CC=CC=1.C(OCC)(=O)C>[Si:13]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](/[CH:28]=[CH:1]/[CH:2]2[N:7]=[CH:6][C:5]3[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:4]=3[S:3]2)[CH:23]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15]

Participants

6

Reactant 2

HCID 156617653-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]BenzaldehydeHCID 190194722-Methyl-6-chloro-1,3-benzthiazine

Product 1

HCID 1317185143-(6-Chloro-1,3-benzthiazin-2-yl-transethenyl)benzyl alcohol t-butyldimethylsilyl ether

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalyst2×HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.08 g of 2-methyl-6-chloro-1,3-benzthiazine 1.51 g of 3-formylbenzyl alcohol t-butyldimethylsilyl ether and 5 drops of piperidine in 60 ml of benzene was heated to reflux in a Dean-Stark trap for 1 hour. An additional 5 drops of piperidine were added and the refluxing continued from 30 hours. The mixture was diluted with 400 ml of ethyl acetate and washed with water (1×40 ml) and brine (1×40 ml). The organic layer was dried over magnesium sulfate and concentrated to 2 g of crude product which was chromatographed on silica gel using 5% ethyl acetate in hexane (v:v), 188 mg, m.p. 58°-60° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux in a Dean-Stark trap for 1 hour
  3. washwashed with water (1×40 ml) and brine (1×40 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated to 2 g of crude product which
  6. customwas chromatographed on silica gel using 5% ethyl acetate in hexane (v:v), 188 mg, m.p. 58°-60° C.

Sources & evidence

ORD record
ord-0249f3a74d674c23a26e9afe34fe8653
Source dataset
uspto-grants-1994_06
Patent number
US05322847

Reaction notes

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