Diethyl Ether → 8-Methoxychromane-6-carbaldehyde

HRID 1903583

Reaction equation

HRID 1903583 reaction equation
Br[C:2]1(OC)[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.C([Li])CCC.CN(C)[CH:21]=[O:22].C[CH2:25][O:26]CC>C(OC(C)C)(C)C>[CH3:25][O:26][C:5]1[CH:6]=[C:7]([CH:21]=[O:22])[CH:8]=[C:9]2[C:4]=1[O:3][CH2:2][CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 3283Diethyl Ether3×HCID 6228DimethylformamideHCID 20193557Bromo-methoxy-chromanHCID 178418339Butyllithium

Product 1

HCID 128319838-Methoxychromane-6-carbaldehydeYield 51%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
-50 °C

Procedure

The procedure is as according to the method described for preparation III, but maintaining the temperature at -50° C. From 186 g (7.7×10-1M) of bromo-methoxy-chroman Ib2 in 500 cm3 of anhydrous ether and 7.7×10-1M of n-butyllithium in 650 cm3 of anhydrous ether, and after addition of 78 g (1.1 M) of N,N-dimethylformamide in 200 cm3 of anhydrous ether and recrystallisation in isopropyl ether, 75 g (yield=51%) of expected compound are isolated. m.p.=81° C.

Sources & evidence

ORD record
ord-f86e1d0a8a474c68a8f22ae9ab89240b
Source dataset
uspto-grants-1984_03
Patent number
US04436915

Linked notes

Loading…