Methane, dichloromethoxy- → 4-Cyclopentyloxydibenzo[b,d]furan-1-carbaldehyde

HRID 1293434Notes

Reaction equation

HRID 1293434 reaction equation
[CH:1]1([O:6][C:7]2[C:12]3[O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:21]([O:23]C)Cl.[Sn](Cl)(Cl)(Cl)Cl.[K+].[Br-]>>[CH:1]1([O:6][C:7]2[C:12]3[O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:11]=3[C:10]([CH:21]=[O:23])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 4

HCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 253877Potassium BromideHCID 692801164-Cyclopentyloxydibenzo[b,d]furan

Product 1

HCID 442251954-Cyclopentyloxydibenzo[b,d]furan-1-carbaldehydeYield 31.5%

Procedure

Reaction of 4-cyclopentyloxydibenzo[b,d]furan (1.0 g, 3.96 mmol) with dichloromethylmethylether (456 mg, 3.96 mmol) in presence of tin(IV)chloride (1.55 g, 5.95 mmol), gave 350 mg (31.5%) of the product as white solid, IR (KBr)) 2960, 2730, 1686, 1565, 1276, 1099 cm−1. 1H NMR (300 MHz, CDCl3) δ 1.64-1.75 (m, 2H), 1.85-1.98 (m, 2H), 2.03-2.09 (m, 4H), 5.11 (quint, 1H), 7.07 (d, J=8.2 Hz, 1H), 7.38 (t, J=7.9H, 1H), 7.52 (t, J=7.8 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.77 (d, J=8.2 Hz, 1H), 8.95 (d, J=8.4 Hz, 1H), 10.17 (s, 1H).

Sources & evidence

ORD record
ord-3906bb4b686146839c7f6f3768d486ce
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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