Tetrahydrofuran → Tert-butyl 2-(diphenylmethyleneamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)hex-5-enoate

HRID 579546Notes

Reaction equation

HRID 579546 reaction equation
[C:1]1([C:7](=[N:14][CH:15]([CH2:23][CH2:24][CH:25]=[CH2:26])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH2:43][CH2:44][CH2:45][CH2:46][B:47]1[O:51][C:50]([CH3:53])([CH3:52])[C:49]([CH3:55])([CH3:54])[O:48]1>C(OCC)C>[C:1]1([C:7](=[N:14][C:15]([CH2:43][CH2:44][CH2:45][CH2:46][B:47]2[O:51][C:50]([CH3:53])([CH3:52])[C:49]([CH3:54])([CH3:55])[O:48]2)([CH2:23][CH2:24][CH:25]=[CH2:26])[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoateHCID 66833241HCID 66833241, compound

Product 1

HCID 86663728Tert-butyl 2-(diphenylmethyleneamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)hex-5-enoateYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

While under an atmosphere of argon, a solution of tert-butyl 2-(diphenylmethyleneamino)hex-5-enoate (7.00 g, 20.06 mmol) in freshly distilled (THF 50 mL) was cooled to −78° C. and treated with sodium bis(trimethylsilyl)amide (60 mL, 1.0 M in THF). After stirring for 10 min 2-(4-iodobutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12.4 g, 40.0 mmol) was added and the reaction was warmed to room temperature and stirred for 16 h. Next, the reaction mixture was cooled to 0° C., diluted with ethyl ether and washed successively with saturated aqueous NaHCO3 and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-20% ethyl acetate in heptane with 0.5% triethylamine over 6 CV) gave tert-butyl 2-(diphenylmethyleneamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)hex-5-enoate as a colorless oil (8.50 g, 80%). Rf 0.55 (30% ethyl acetate in heptane). ESI MS found for C33H46BNO4 m/z [532.5 (M+1)].

Workup

  1. additionwas added
  2. temperaturethe reaction was warmed to room temperature
  3. temperatureNext, the reaction mixture was cooled to 0° C.
  4. washwashed successively with saturated aqueous NaHCO3 and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by MPLC (1-20% ethyl acetate in heptane with 0.5% triethylamine over 6 CV)

Sources & evidence

ORD record
ord-32e636f03add49a385ec56e55219b5de
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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