1-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone → HCID 14329735, compound
Reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH:6]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:8]=2[O:7]1)C.Br[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=1[CH2:33][CH2:34][CH3:35]>>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][CH2:19][O:16][C:14]2[CH:13]=[CH:12][C:9]3[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:3])=[O:17])[O:7][C:8]=3[CH:15]=2)=[C:24]([CH2:33][CH2:34][CH3:35])[C:25]=1[OH:32])(=[O:31])[CH3:30]Participants
Procedure
A 0.9 g sample of racemic-3,4-dihydro-7-hydroxy-2H-1-benzopyran-2-acetic acid ethyl ester was alkylated with 3 g of 4'-(3-bromopropoxy)-2'-hydroxy-3'-n-propylacetophenone using the procedure described in Example 31. The crude product (2.6 g ) was chromatographed on 50 g of silica gel giving 1.2 g of the desired ester as a pale-yellow oil (eluted with 19:1 toluene-ethyl acetate). This material was saponified with 2.0 g of lithium hydroxide monohydrate using the procedure described in Example 31. The crude acid (1.1 g) was chromatographed on 50 g of silica gel. Elution with 2:1 and 1:1 toluene-ethyl acetate afforded 682 mg (40.5%) of racemic-7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3,4-dihydro-2H-1-benzopyran-2-acetic acid as a pale-yellow solid, mp 107°-109.5° C.
Workup
- customThe crude product (2.6 g ) was chromatographed on 50 g of silica gel giving 1.2 g of the desired ester as a pale-yellow oil (eluted with 19:1 toluene-ethyl acetate)
- customThe crude acid (1.1 g) was chromatographed on 50 g of silica gel
- washElution with 2:1 and 1:1 toluene-ethyl acetate
Sources & evidence
- ORD record
- ord-da16808c7f6746f8813d8997bbfaaa7a
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04788214
Reaction notes
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