HCID 11183526, compound → HCID 15488936, compound

HRID 2304846Notes

Reaction equation

HRID 2304846 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]([O:32][Si:33]([CH2:38][CH3:39])([CH2:36][CH3:37])[CH2:34][CH3:35])([C:28]([F:31])([F:30])[F:29])/[CH:4]=[CH:5]\[CH2:6][C:7]([CH3:27])([CH3:26])[CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13]S(C1SC2C=CC=CC=2N=1)(=O)=O.[Li]N([Si](C)(C)C)[Si](C)(C)C.[C:52]([O:55][C@@H:56]1[CH2:61][CH:60](O)[CH2:59][C@@H:58]([O:63][C:64](=[O:66])[CH3:65])[CH2:57]1)(=[O:54])[CH3:53]>C1COCC1>[C:52]([O:55][C@@H:56]1[CH2:61][C:60](=[CH:13]/[CH:12]=[CH:11]/[CH2:10][CH2:9][CH2:8][C:7]([CH3:27])([CH3:26])[CH2:6]/[CH:5]=[CH:4]\[C:3]([O:32][Si:33]([CH2:38][CH3:39])([CH2:34][CH3:35])[CH2:36][CH3:37])([C:2]([F:1])([F:40])[F:41])[C:28]([F:31])([F:30])[F:29])[CH2:59][C@@H:58]([O:63][C:64](=[O:66])[CH3:65])[CH2:57]1)(=[O:54])[CH3:53]

Participants

5

Reactant 3

HCID 11183526HCID 11183526, compoundHCID 11422337HCID 11422337, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 15488936HCID 15488936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 322 mg of (2E,9Z)-2-(12,12,12-Trifluoro-7,7-dimethyl-11-triethylsilanyloxy-11-trifluoromethyl-dodeca-2,9-diene-1-sulfonyl)-benzothiazole in 2 ml of THF was added at −78° 0.5 ml of LiN(SiMe3)2 (1.0 M in THF) and stirring of the red solution was continued for 30 min. To this solution was added at −78° a solution of 107 mg of (1R,3R)-1,3-diacetoxy-5-hydroxy-cyclohexane in 1 ml of THF over 10 min and stirring was continued for 5 h after which time t.l.c. indicated almost completion of the reaction. The mixture was warmed to 22°, washed with sat. aqueous NH4Cl-solution, the organic layer was dried over MgSO4 and evaporated. The residue was chromatographed on a Lobar CN-column (Merck) with CH2Cl2/CH3CN/hexane 15:5:200 to give 230 mg of the pure (t.l.c.) title compound as a colorless oil. IR (neat): 1735 m (CO); MS (El): 613/1 (M−C2H5).

Workup

  1. stirringstirring
  2. waitwas continued for 5 h
  3. customcompletion of the reaction
  4. temperatureThe mixture was warmed to 22°
  5. washwashed with sat. aqueous NH4Cl-solution
  6. dry with materialthe organic layer was dried over MgSO4
  7. customevaporated
  8. customThe residue was chromatographed on a Lobar CN-column (Merck) with CH2Cl2/CH3CN/hexane 15:5:200

Sources & evidence

ORD record
ord-f1c900a31d104c65b8a4bd10b88ae853
Source dataset
uspto-grants-2002_08
Patent number
US06437142B1

Reaction notes

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