Benzyl Alcohol → HCID 89714609, compound

HRID 2273064Notes

Reaction equation

HRID 2273064 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[C:22]2[C:21](=[O:23])[N:20]([CH2:24][CH3:25])[CH2:19][C:18]([CH3:27])([CH3:26])[O:17][C:16]=2[N:15]=[C:14]([S:28][CH3:29])[N:13]=1.O>C1COCC1>[CH2:1]([O:8][C:12]1[C:22]2[C:21](=[O:23])[N:20]([CH2:24][CH3:25])[CH2:19][C:18]([CH3:26])([CH3:27])[O:17][C:16]=2[N:15]=[C:14]([S:28][CH3:29])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 89714606HCID 89714606, compound

Product 1

HCID 89714609HCID 89714609, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

6.20 ml of benzyl alcohol (59.64 mmol) are placed in 400 ml of anhydrous THF. The solution is cooled to 4° C. in an ice bath and 2.39 g of 60% sodium hydride (59.64 mmol) are added portionwise. The reaction mixture is stirred at 4° C. for 15 minutes. 15 g of 4-chloro-6-ethyl-8,8-dimethyl-2-methylsulfanyl-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzo cyclohepten-5-one (49.70 mmol) dissolved in 400 ml of anhydrous THF are added dropwise. After stirring for 2 hours at 4° C., 400 ml of water are added and the THF is evaporated off. The aqueous phase is extracted twice with 300 ml of DCM, and the organic phases are combined and washed with 400 ml of water and then 400 ml of brine. The organic phase is dried over Na2SO4, filtered and concentrated. The residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 30% to 50%. 18.6 g of 4-benzyloxy-6-ethyl-8,8-dimethyl-2-methylsulfanyl-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzocyclohepten-5-one are obtained.

Workup

  1. additionare added dropwise
  2. stirringAfter stirring for 2 hours at 4° C.
  3. customthe THF is evaporated off
  4. extractionThe aqueous phase is extracted twice with 300 ml of DCM
  5. washwashed with 400 ml of water
  6. dry with materialThe organic phase is dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 30% to 50%

Sources & evidence

ORD record
ord-1783938c3fe0405887de321d3f48c807
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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