Water → HCID 12399387, compound

HRID 1180760Notes

Reaction equation

HRID 1180760 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li]CCCC.[C:15]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16]1.O>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:15]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 7222BenzothiazoleHCID 8452CyclopentanoneHCID 178418339Butyllithium

Product 1

HCID 12399387HCID 12399387, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2 mL (18.3 mmol) of benzothiazole in 20 mL of tetrahydrofuran was added 11.4 mL (18.2 mmol) of 1.6 M n-BuLi at −78° C. After 45 min, 1.6 mL (18.1 mmol) of cyclopentanone was added at the same temperature. The reaction was let warm to room temperature over 1 h. Water was added to quench the reaction and the mixture was extracted with ether (3×). The ether layer was washed with brine (3×) and dried over magnesium sulfate. After removal of solvent, purification by silica gel column chromatography eluting with hexane:ethyl acetate (4:1) gave 2.8 g (71%) of 1-(1,3-benzothiazol-2-yl)cyclopentanol as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.02 (d, J=8 Hz, 1H), 7.92 (d, J=8 Hz, 1H), 7.51 (t, J=8 Hz, 1H), 7.41 (t, J=8 Hz, 1H), 2.25 (m, 4H), 2.00 (m, 4H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ether (3×)
  4. washThe ether layer was washed with brine (3×)
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of solvent, purification by silica gel column chromatography
  7. washeluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-697e209a037a44a5bf26c6725d134078
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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