Benzyl Alcohol → 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(4-benzyloxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran

HRID 358606Notes

Reaction equation

HRID 358606 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([N:15]3[CH2:19][C:18]([O:20][CH3:21])=[CH:17][C:16]3=[O:22])[C:7]=2[CH:23]=1)#[N:2].C(O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CS(O)(=O)=O>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([N:15]3[CH2:19][C:18]([O:20][CH2:21][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:17][C:16]3=[O:22])[C:7]=2[CH:23]=1)#[N:2]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 6395Methanesulfonic AcidHCID 679241126-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(4-methoxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran

Product 1

HCID 150075876-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(4-benzyloxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran

Procedure

Alternatively, a mixture of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(4-methoxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran (0.7 g), benzyl alcohol (0.92 ml) and methanesulfonic acid (0.01 g) was refluxed for 2 hours in the presence of 3A molecular sieves. After cooling the molecular sieves were filtered off, the filtrate stirred with diethylether, the insoluble product filtered off and washed twice with diethylether, to give 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(4-benzyloxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran, m.p. 248° C.

Workup

  1. temperatureAfter cooling the molecular sieves
  2. filtrationwere filtered off
  3. filtrationthe insoluble product filtered off
  4. washwashed twice with diethylether

Sources & evidence

ORD record
ord-ee9420a5e32445b187d263b08989b664
Source dataset
uspto-grants-1991_03
Patent number
US04997846

Reaction notes

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