Hexane → HCID 68545185, compound

HRID 1432087Notes

Reaction equation

HRID 1432087 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8](S(C1C=CC=CC=1)(=O)=O)[CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])([CH3:4])([CH3:3])[CH3:2].[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[O-:30].[Li+].C[Si](N[Si](C)(C)C)(C)C.[Li]CCCC.CCCCCC.O1CC=CC1=O>C1COCC1.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH:29]1[CH:28]=[CH:27][C:26](=[O:30])[O:25]1)[CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])([CH3:2])([CH3:3])[CH3:4]

Participants

10

Reactant 6

HCID 8058HexaneHCID 103412(5H)-FuranoneHCID 13838HexamethyldisilazaneHCID 68538892HCID 68538892, compoundHCID 68540939HCID 68540939, compoundHCID 178418339Butyllithium

Product 1

HCID 68545185HCID 68545185, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-75 °C

Procedure

A solution of 17.15 g (46.7 mmol) of ((R)-1-benzenesulfonyl-3-methyl-hex-5-enyl)-carbamic acid tert-butyl ester in 100 ml dry THF under nitrogen atmosphere is cooled to −75° C. A solution A containing lithium furan-2-olate in THF is added over a period of 10 minutes via a canula using positive nitrogen pressure. Solution A is prepared as follows. A solution of 9.85 ml (46.7 mmol) HMDS in 100 ml dry THF under nitrogen atmosphere is cooled at −70° C. and 29.2 ml of a 1.6 M solution of BuLi in hexane (46.7 mmol) are added dropwise. After 30 minutes 3.92 g (46.7 mmol) 5H-furan-2-one in 2 ml dry THF are added dropwise and the temperature is kept at −40° C. After addition the reaction mixture is stirred at −75° C. for 1.5 h and then poured directly, with stirring, in 200 ml water and 200 ml EtOAc. The organic phase is washed successively with 5% aqueous citric acid, water (2×), 5% aqueous NaHCO3 solution and water (4×). The reaction mixture is evaporated and the residue chromatographed over silica gel (EtOAc/hexane 1:3) to yield the title compound as an oil.

Workup

  1. customis kept at −40° C
  2. additionAfter addition the reaction mixture
  3. additionpoured directly
  4. washThe organic phase is washed successively with 5% aqueous citric acid, water (2×), 5% aqueous NaHCO3 solution and water (4×)
  5. customThe reaction mixture is evaporated
  6. customthe residue chromatographed over silica gel (EtOAc/hexane 1:3)

Sources & evidence

ORD record
ord-08b073fe9ba94a82af282675479a8e35
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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