1,2-Naphthoquinone → HCID 57661828, compound

HRID 1665425Notes

Reaction equation

HRID 1665425 reaction equation
[SH:1][CH2:2][C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:10]1(=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]1=[O:20]>>[O:9]1[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2][S:1][C:12]2[C:11](=[O:20])[C:10](=[O:21])[C:19]3[C:14]([C:13]1=2)=[CH:15][CH:16]=[CH:17][CH:18]=3

Participants

3

Reactant 2

HCID 106671,2-NaphthoquinoneHCID 86629710HCID 86629710, compound

Product 1

HCID 57661828HCID 57661828, compound

Procedure

The crude 1-(mercaptomethyl)cyclohexanol was then reacted with naphthalene-1,2-dione as outlined in procedure F [both step (i) and (ii)] to afford crude spiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione. The crude spiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione was purified by flash column chromatography (SiO2, 100% dichloromethane) to afford the product (0.183 g) as a purple solid. M.p.=194-195° C., 400 MHz 1H NMR CDCl3 δ 8.05-8.0 (m, 1H), 7.8-7.72 (m, 1H), 7.68-7.6 (m, 1H), 7.5-7.4 (m, 1H), 2.91 (s, 2H), 2.15-2.0 (m, 2H), 1.8-1.53 (m, 7H), 1.5-1.35 (m, 1H); LCMS=301 [M+H].

Workup

  1. customto afford crude spiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione
  2. customThe crude spiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione was purified by flash column chromatography (SiO2, 100% dichloromethane)

Sources & evidence

ORD record
ord-7a1b9115ad61416ea1514e5fa07dcd20
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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