2-(3-Bromophenoxy)tetrahydro-2H-pyran → 1-{4-[2-(2-Benzyloxyethoxy)ethoxy]phenyl}-2-phenyl-4-(tetrahydropyran-2-yloxy)-1-[3-(tetrahydropyran-2-yloxy)phenyl]butan-1-ol

HRID 1368952Notes

Reaction equation

HRID 1368952 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:38])[CH:22]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1[O:45][C:46]1[CH:47]=[C:48](Br)[CH:49]=[CH:50][CH:51]=1>>[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:50]2[CH:49]=[CH:48][CH:47]=[C:46]([O:45][CH:40]3[CH2:41][CH2:42][CH2:43][CH2:44][O:39]3)[CH:51]=2)([OH:38])[CH:22]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 50672642-(3-Bromophenoxy)tetrahydro-2H-pyranHCID 225046131-{4-[2-(2-Benzyloxyethoxy)ethoxy]phenyl}-2-phenyl-4-(tetrahydropyran-2-yloxy)butan-1-one

Product 1

HCID 225045341-{4-[2-(2-Benzyloxyethoxy)ethoxy]phenyl}-2-phenyl-4-(tetrahydropyran-2-yloxy)-1-[3-(tetrahydropyran-2-yloxy)phenyl]butan-1-ol

Procedure

is prepared by using the method described in the example 4e starting from 1-{4-[2-(2-benzyloxyethoxy)ethoxy]phenyl}-2-phenyl-4-(tetrahydropyran-2-yloxy)butan-1-one (10 g, 19.2 mmol) and 3-(tetrahydropyran-2-yloxy)phenyl bromide (9.8 g, 38 mmol). The product is purified by flash chromatography with toluene-methanol (50:1) as eluent. Yield 5.7 g, 43%.

Workup

  1. customis prepared
  2. customThe product is purified by flash chromatography with toluene-methanol (50:1) as eluent

Sources & evidence

ORD record
ord-f44d7abc0fd64749ad0b1b6f25c6d7a2
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

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