Tetrahydrofuran → Isohexane ethyl acetate

HRID 658339Notes

Reaction equation

HRID 658339 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:19]=O)[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[N:11][C:10]=2[CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>ClCCl>[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH2:22])[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[N:11][C:10]=2[CH:18]=1)([CH3:2])([CH3:3])[CH3:4].[C:22]([O:21][CH2:25][CH3:24])(=[O:5])[CH3:23].[CH3:18][CH2:6][CH2:7][CH:8]([CH3:19])[CH3:9]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 866198325-Tert-butoxy-2-isopropoxybenzo[d]thiazole-7-carbaldehyde

Product 2

HCID 21882781Isohexane ethyl acetateHCID 667441865-(Tert-butoxy)-2-isopropoxy-7-vinylbenzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ph3PMe.Br (5.0 g) is dissolved in dry tetrahydrofuran (100 ml) under argon. N-butyl lithium (8.8 ml, of 1.6 M solution) is added at room temperature over 10 minutes and reaction mixture stirred for a further 30 minutes. A solution of 5-tert-Butoxy-2-isopropoxy-benzothiazole-7-carbaldehyde (1.25 g) in dichloromethane (40 ml) is added drop wise to the reaction mixture and the reaction mixture is stirred for 4.5 hours at room temperature. The solvent is removed in vacuo, redissolved in ethyl acetate, washed with water (3×), brine (1×), dried over MgSO4, filtered and the solvent removed in vacuo. The title compound is obtained by flash column chromatography (silica, eluent ethyl acetate/iso-hexane 1:9). MS (ES+) m/e 292 (MH+) LCT55980

Workup

  1. customreaction mixture
  2. stirringthe reaction mixture is stirred for 4.5 hours at room temperature
  3. customThe solvent is removed in vacuo
  4. dissolutionredissolved in ethyl acetate
  5. washwashed with water (3×), brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ef323dbbe8b84368bbcd41d7baaff068
Source dataset
uspto-grants-2011_12
Patent number
US08076489B2

Reaction notes

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