HCID 131714001, compound → HCID 131713999, compound

HRID 1905121Notes

Reaction equation

HRID 1905121 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[CH2:25]([O:32][CH:33]1[C:38]([CH2:40][C:41]#[N:42])(O)[C:37]2[CH:43]=[CH:44][C:45]([O:47][CH:48]([CH2:50][CH2:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH3:49])=[CH:46][C:36]=2[O:35][C:34]1([CH3:60])[CH3:59])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.CS(O)(=O)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[CH2:25]([O:32][CH:33]1[C:38](=[CH:40][C:41]#[N:42])[C:37]2[CH:43]=[CH:44][C:45]([O:47][CH:48]([CH2:50][CH2:51][CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH3:49])=[CH:46][C:36]=2[O:35][C:34]1([CH3:59])[CH3:60])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 131714001HCID 131714001, compound

Product 1

HCID 131713999HCID 131713999, compoundYield 13.6%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 11.5 g (23.7 mmole) dl-5-benzyloxy-4-cyanomethyl-4-hydroxy-2,2-dimethyl-7-(5-phenyl-2-pentyloxy)-3,4-dihydro-2H-benzopyran in 100 ml dry toluene was added a few grams of molecular sieves and 5 drops of methanesulfonic acid. The mixture was stirred for 16 hours at room temperature, washed with 30 ml water, 2×30 ml saturated sodium bicarbonate solution, dried (MgSO4), filtered and the filtrate evaporated in vacuo to afford a yellow oil. Trituration with ethyl ether, filtration gave 2.60 g colorless solid. Evaporation of the mother liquor to half-volume and addition of petroleum ether afforded a second crop, 3.75 g. Total yield: 6.35 g (60.4%).

Workup

  1. washwashed with 30 ml water, 2×30 ml saturated sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo
  5. customto afford a yellow oil
  6. filtrationTrituration with ethyl ether, filtration

Sources & evidence

ORD record
ord-9c981dd71ffa4b83b4311ab9aadcc8dc
Source dataset
uspto-grants-1989_06
Patent number
US04841078

Reaction notes

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