6-Bromo-1,4-benzodioxane → HCID 69205409, compound

HRID 970964Notes

Reaction equation

HRID 970964 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Br[C:14]1[CH:23]=[CH:22][C:17]2[O:18][CH2:19][CH2:20][O:21][C:16]=2[CH:15]=1.C([Li])CCC.O1C2C=CC(C(C3C=C(OC)C=C(OC)C=3)O)=CC=2OCC1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]([C:14]3[CH:23]=[CH:22][C:17]4[O:18][CH2:19][CH2:20][O:21][C:16]=4[CH:15]=3)[OH:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 1041416-Bromo-1,4-benzodioxaneHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanolHCID 178418339Butyllithium

Product 1

HCID 69205409HCID 69205409, compoundYield 86.4%

Procedure

2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde (0.87 g, 5.28 mmol), 6-bromo-2,3-dihydrobenzo[1,4]dioxine (1.25 g, 5.81 mmol), and n-butyl lithium (2.33 ml, 5.81 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.) to give bis-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanol as an oil (1.37 g, 86%): 1HNMR (CDCl3) 6.87-6.82 (m, 6H, Ar), 5.63 (d, J=3 Hz, 1H, CHOH), 4.22 (s, 8H, 2CH2CH2), 2.19 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Workup

  1. customThe crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record
ord-4381e5b59605420e8d7811634eaa68cf
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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