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

HRID 537632Notes

Reaction equation

HRID 537632 reaction equation
COC1C=CC(C2(C3C=CC(OC)=CC=3)O[C:13]3[C:15]4[C:20]([C:21](C5C=CC=CC=5)=[C:22]([C:23](OCCO)=[O:24])[C:12]=3C=C2)=[CH:19][CH:18]=[CH:17][CH:16]=4)=CC=1.C(N([CH2:48][CH3:49])CC)C>C(OCC)C>[CH:12]1[C:13]2[C:15]3[C:20]([CH:21]=[CH:48][C:49]=2[O:24][CH2:23][CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 23298978HCID 23298978, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,2-Bis(4-methoxyphenyl)-5-(2-hydroxyethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran (U.S. Pat. No. 6,113,814) (0.20 g, 0.34 mmol) was dissolved in anhydrous diethyl ether (20 ml) under nitrogen. To this solution was added triethylamine (0.2 ml) followed by the Acid Chloride Terminated Polydimethylsiloxane (Example 1, Step 2) (0.264 g), dropwise. The mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the crude product then purified by column chromatography (silica gel, diethyl ether/hexane, 5:1) giving the bulk product, Naphthopyran Terminated Polydimethylsiloxane, as a pink tar. Analysis by 1H NMR gave a spectrum consistent with the structure, having an average molecular weight (Mn) of 2,592 (nPDMS=14.1).

Workup

  1. customTerminated Polydimethylsiloxane (Example 1, Step 2) (0.264 g)
  2. customThe solvent was evaporated
  3. customthe crude product then purified by column chromatography (silica gel, diethyl ether/hexane, 5:1)

Sources & evidence

ORD record
ord-bd1c75c11332417aac1ce93965fb3aa9
Source dataset
uspto-grants-2014_10
Patent number
US08865029B2

Reaction notes

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