1,2-Naphthoquinone → HCID 57661968, compound

HRID 1665426Notes

Reaction equation

HRID 1665426 reaction equation
[SH:1][CH2:2][C:3]1([OH:9])[CH2:8][CH2:7][O: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:6]1[CH2:7][CH2:8][C:3]2([O:9][C:13]3[C:14]4[C:19]([C:10](=[O:21])[C:11](=[O:20])[C:12]=3[S:1][CH2:2]2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 106671,2-NaphthoquinoneHCID 86629711HCID 86629711, compound

Product 1

HCID 57661968HCID 57661968, compound

Procedure

The crude 4-(mercaptomethyl)tetrahydro-2H-pyran-4-ol was then reacted with naphthalene-1,2-dione as outlined in procedure F [both step (i) and (ii)] to afford crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-pyran]-5,6-dione. The crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-pyran]-5,6-dione was purified by flash column chromatography (SiO2, 100% dichloromethane) to afford the product as a purple solid. M.p.=195-197° C.; 400 MHz 1H NMR (CDCl3) δ: 8.06 (dd, J=7.6 1.0 Hz, 1H), 7.79 (dd, J=7.6 0.8 Hz, 1H), 7.67 (td, J=8.0 1.6 Hz 1H), 7.50 (td, J=8.0 1.2 Hz, 1H), 3.96-3.83 (m, 4H), 2.97 (s, 2H), 2.10-2.05 (m, 2H), 1.95-1.87 (m, 2H); LCMS: 303 [M+H].

Workup

  1. customto afford crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-pyran]-5,6-dione
  2. customThe crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-pyran]-5,6-dione was purified by flash column chromatography (SiO2, 100% dichloromethane)

Sources & evidence

ORD record
ord-34067bfd0281407284eebf54ce1807d3
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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