5,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(4-trifluoromethylbenzamido)-7H-thieno[3,2-b]pyran → HCID 14986526, compound

HRID 981503Notes

Reaction equation

HRID 981503 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][CH:10]2[CH:15]([OH:16])[C:14]([CH3:18])([CH3:17])[O:13][C:12]3[CH:19]=[CH:20][S:21][C:11]2=3)=[O:8])=[CH:5][CH:4]=1>Cl(O)(=O)(=O)=O.C(OC(=O)C)(=O)C>[C:7]([O:16][CH:15]1[C:14]([CH3:18])([CH3:17])[O:13][C:12]2[CH:19]=[C:20]([C:12](=[O:13])[CH3:11])[S:21][C:11]=2[CH:10]1[NH:9][C:7](=[O:8])[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:24])[F:25])=[CH:23][CH:22]=1)(=[O:8])[CH3:6]

Participants

4

Reactant 1

HCID 149865085,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(4-trifluoromethylbenzamido)-7H-thieno[3,2-b]pyran

Product 1

HCID 14986526HCID 14986526, compound

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

The title compound was prepared as described in Example 6 starting with 7-(4-trifluoromethylbenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran (1.5 g, 4.04 mmol), perchloric acid (70%, 10 drops) and acetic anhydride (20 ml) to give the product after crystallization from dichloromethane and hexanes 0.382 g (21%) as a colorless solid; mp 225°-227° C.; IR (KBr):1755, 1668, 1654, 1541 and 1471 cm-1 ; MS=m/z 456 (MH+);1H NMR (CDCl3): δ 1.41(s,3H), 1.43 (s,3H), 2.13 (s,3H), 2.47 (s,3H), 5.17 (d,J=9.3 Hz,1H), 5.42(m,1H), 6.77 (bd,J=7.9 Hz,1H), 7.14 (s,1H), 7.72 (d,J=8.3 Hz, 2H) and 7.88 (d,J=8.3 Hz,2H).

Workup

  1. customto give the product
  2. customafter crystallization from dichloromethane and hexanes 0.382 g (21%) as a colorless solid

Sources & evidence

ORD record
ord-f5f8f1121eeb457c9b5abaf79f2f1962
Source dataset
uspto-grants-1991_02
Patent number
US04992435

Reaction notes

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