Triethylamine → HCID 131737167, compound

HRID 61314Notes

Reaction equation

HRID 61314 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([CH2:17][OH:18])([CH2:12][O:13][CH2:14][CH:15]=[CH2:16])[CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:26]1([CH:34]=[CH:35][C:36](Cl)=[O:37])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]=1>C1(C)C=CC=CC=1>[CH2:9]([O:8][CH2:7][C:6]([CH2:17][OH:18])([CH2:12][O:13][CH2:14][CH:15]=[CH2:16])[CH2:5][O:4][CH2:1][CH:2]=[CH2:3])[CH:10]=[CH2:11].[C:26]1([CH:34]=[CH:35][C:36]([OH:37])=[O:4])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738543-(Allyloxy)-2,2-bis((allyloxy)methyl)propanolHCID 178521137HCID 178521137, compound

Product 1

HCID 131737167HCID 131737167, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

A 1000 mL three necked round bottomed flask outfitted with a mechanical stirrer (Teflon paddle), a pressure equalizing addition funnel was charged with pentaerythritol triallyl ether (NEOALLYL P-30) (111.9 g, 436.5 mmol), toluene (300 mL) and triethylamine (56.61 g, 559.4 mmol). The addition funnel was charged with a solution of BCB-AA acid chloride (88.96 g, 461.8 mmol) from Example 6 in toluene (100 mL), which was then added dropwise to the reaction mixture over 45 min. The solution was then heated to 90° C. for 9.5 hr. The solution was then filtered through a 38 mm (1.5 inch) thick silica gel plug on a 350 mL fritted glass funnel. Hexane:ethyl acetate (80:20, 200 mL) was used as the washing solvent. The filtrate was condensed to afford an orange colored viscous oil, which was taken up in hexanes (300 mL) and placed into a freezer for 3 days. The solution was filtered and condensed to afford the product as a viscous dark yellow colored oil. Yield: 178.0 g (93.97%). 1H NMR (500 MHz, Chloroform-d) δ 7.67 (dd, J=15.9, 3.1 Hz, 1H), 7.36 (dd, J=7.6, 1.5 Hz, 1H), 7.31-7.18 (m, 1H), 7.13-6.94 (m, 1H), 6.39 (d, J=16.0 Hz, 1H), 5.97-5.78 (m, 2H), 5.27 (dd, J=17.3, 1.7 Hz, 2H), 5.15 (dd, J=10.5, 1.6 Hz, 2H), 4.30 (s, 2H), 3.97 (d, J=5.4 Hz, 4H), 3.52 (s, 4H), 3.20 (s, 3H).

Workup

  1. additionaddition funnel
  2. additionwas then added dropwise to the reaction mixture over 45 min
  3. filtrationThe solution was then filtered through a 38 mm (1.5 inch) thick silica gel plug on a 350 mL fritted glass funnel
  4. customcondensed
  5. customto afford an orange colored viscous oil, which
  6. filtrationThe solution was filtered
  7. customcondensed

Sources & evidence

ORD record
ord-9a3fb7e99e4849269a1ec91b33845405
Source dataset
uspto-grants-2016_09
Patent number
US09441055B1

Reaction notes

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