Triethylamine → 3H-Naphtho[2,1-b]pyran

HRID 537631Notes

Reaction equation

HRID 537631 reaction equation
COC1C=CC(C2(C3C=CC(OC)=CC=3)O[C:13]3[C:15]4[C:20]([C:21](O)=[C:22]([C:23](OC)=[O:24])[C:12]=3C=C2)=[CH:19][CH:18]=[CH:17][CH:16]=4)=CC=1.C(N([CH2:41][CH3:42])CC)C>C1COCC1>[CH:12]1[C:13]2[C:15]3[C:20]([CH:21]=[CH:41][C:42]=2[O:24][CH2:23][CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 6618057HCID 6618057, compound

Product 1

HCID 123289773H-Naphtho[2,1-b]pyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2-Bis(4-methoxyphenyl)-5-(methoxycarbonyl)-6-hydroxy-[2H]-naphtho[1,2-b]pyran (U.S. Pat. No. 5,458,814) (0.225 g, 0.48 mmol) was dissolved in anhydrous THF (25 ml) under nitrogen. To this solution was added triethylamine (0.13 ml) followed by the Acid Chloride Terminated Polydimethylsiloxane (Example 1, Step 2) (0.358 g), dropwise. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered through a short plug of silica gel and the solvent evaporated. The crude product (0.53 g) was then purified by column chromatography (silica gel, diethyl ether/hexane, 2:3→2:1) giving the bulk product, Naphthopyran Terminated Polydimethylsiloxane, as a viscous red oil. Analysis by 1H NMR gave an average molecular weight (Mn) of 2,297 (nPDMS=12.6). 1H NMR (200 MHz, d6-acetone) δ 8.40 (m, 2H), 7.95 (m, 2H), 7.63 (m, 4H), 7.45 (m, 8H), 6.97 (d, 2H), 6.88 (m, 8H), 6.41 (d, 2H), 4.23 (t, 4H), 3.95 (s, 6H), 3.75 (s, 12H), 3.62 (t, 4H), 3.41 (t, 4H), 3.04 (m, 4H), 2.80 (m, 4H), 1.60 (m, 4H), 0.58 (m, 4H), 0.13-0.08 (m, SiCH3).

Workup

  1. customTerminated Polydimethylsiloxane (Example 1, Step 2) (0.358 g)
  2. filtrationThe reaction mixture was filtered through a short plug of silica gel
  3. customthe solvent evaporated
  4. customThe crude product (0.53 g) was then purified by column chromatography (silica gel, diethyl ether/hexane, 2:3→2:1)

Sources & evidence

ORD record
ord-e883cb766c85403ba73de2d369f95570
Source dataset
uspto-grants-2014_10
Patent number
US08865029B2

Reaction notes

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