Hexane → HCID 14459926, compound

HRID 346198Notes

Reaction equation

HRID 346198 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]([C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](CC)CC)C.CCCCCC.C(OCC)(=O)C>FC(F)(F)C(O)=O.O>[C:1]1([CH2:7][CH2:8][CH2:9][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 14459942HCID 14459942, compound

Product 1

HCID 14459926HCID 14459926, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the title product of Example 39 (2.0 g, 5.9 mmol) in trifluoroacetic acid (20 ml), cooled to 0° C., was treated with triethylsilane (2.8 ml, 18 mmol). After 25 minutes at 0° C., the solution was diluted with water (60 ml) and extracted with ether (2×50 ml). The combined extracts were washed with water (2×50 ml) and brine (50 ml), dried over sodium sulfate and concentrated in vacuo, leaving a brown oil. Present title product was isolated by flash-chromatography (hexane:ethyl acetate, 5:1) as an oil (1.11 g, 58%).

Workup

  1. extractionextracted with ether (2×50 ml)
  2. washThe combined extracts were washed with water (2×50 ml) and brine (50 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customleaving a brown oil

Sources & evidence

ORD record
ord-408ae032413943c4977f0124db46e620
Source dataset
uspto-grants-1991_10
Patent number
US05061717

Reaction notes

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