Diethyl Ether → 7-(Hydroxyphenylmethyl)-3-methoxymethoxy-2-phenyl-6-azabenzo[b]thiophene

HRID 1200016Notes

Reaction equation

HRID 1200016 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]2[CH:19]=[CH:18][N:17]=[CH:16][C:7]=2[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC[O:22][CH2:23][CH3:24]>>[OH:22][CH:23]([C:24]1[CH:7]=[CH:6][CH:5]=[CH:9][CH:10]=1)[C:16]1[C:7]2[S:8][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:6]=2[CH:19]=[CH:18][N:17]=1

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 14277639HCID 14277639, compound

Product 1

HCID 146738217-(Hydroxyphenylmethyl)-3-methoxymethoxy-2-phenyl-6-azabenzo[b]thiopheneYield 44%

Procedure

A solution of 1.0 g (3.7 mmol) of 3-methoxymethoxy-2-phenyl-6-azabenzo[b]thiophene in 5 mL of dry ether was added and the solution was kept at -60° C. for 3 hours. The reaction was quenched with 0.5 mL of benzaldehyde and allowed to warm to room temperature. The mixture was partitioned between ether and water and the aqueous layer was washed with ether. The combined extracts were dried and concentrated to an oil. Chromatography on silica gel (30% ethyl acetate-hexane) afforded 0.62 g (44%) of a colorless oil, NMR (200 MHz, CDCl3) δ3.4 (s, 3H), 5.0 (s, 2H), 5.95 (s, 1H, --OH), 7.2-7.8-(m, 12H), 8.52 (d, J=6 Hz, 1H), Mass Spec m/e 377 (M+).

Workup

  1. customThe reaction was quenched with 0.5 mL of benzaldehyde
  2. customThe mixture was partitioned between ether and water
  3. washthe aqueous layer was washed with ether
  4. customThe combined extracts were dried
  5. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-7f7f1a5c27f8420482ceceac2adea2bb
Source dataset
uspto-grants-1990_02
Patent number
US04904672

Reaction notes

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