7-Chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carbaldehyde → 1-(6-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-8-yl)ethanol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[CH3:14][Mg+].[Br-]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([OH:13])[CH3:14])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
7-Chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carbaldehyde (0.26 g, 1.32 mmol) was dissolved in 10 mL of diethyl ether and cooled to 0° C. MeMgBr (1.1 mL, 3.31 mmol) was added to the solution and the ice bath was removed. The reaction was allowed to stir at rt for 10 min. and at reflux for 30 min. The reaction was cooled to 0° C. and 10 mL of sat NH4Cl were added to quench the reaction. The diethyl ether layer was separated and washed with water (20 mL×2). The organic layer was dried over Na2SO4 and the solvent was removed by rotary evaporation to collect the desired product (258 mg, 91%). 1H NMR (400 MHz, CDCl3): δ 6.91 (s, 1H), 6.77 (s, 1H), 5.02 (m, 1H), 4.24 (m, 4H), 1.45 (d, 3H).
Workup
- customthe ice bath was removed
- temperatureat reflux for 30 min
- temperatureThe reaction was cooled to 0° C.
- addition10 mL of sat NH4Cl were added
- customto quench
- customthe reaction
- customThe diethyl ether layer was separated
- washwashed with water (20 mL×2)
- dry with materialThe organic layer was dried over Na2SO4
- customthe solvent was removed by rotary evaporation
- customto collect the desired product (258 mg, 91%)
Sources & evidence
- ORD record
- ord-37f4f94c15b546b88680f69f8c4fc150
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968538B2
Reaction notes
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