Tetrahydrofuran → HCID 86594387, compound

HRID 2428055Notes

Reaction equation

HRID 2428055 reaction equation
[Li+].CC([N-]C(C)C)C.C(O[O:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22])(=O)CC.[Si:23]([O:30][CH2:31][CH2:32][CH2:33][C@@H:34]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[C@H:35]([CH3:38])[CH:36]=[O:37])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].[CH2:49]1C[O:52][CH2:51][CH2:50]1>>[Si:23]([O:30][CH2:31][CH2:32][CH2:33][C@@H:34]([O:39][CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=1)[C@H:35]([CH3:38])[C@@H:36]([OH:37])[C@@H:50]([CH3:49])[C:51]([O:14][C:15]1[C:16]([CH3:22])=[CH:17][CH:18]=[CH:19][C:20]=1[CH3:21])=[O:52])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 10861826HCID 10861826, compoundHCID 21923459HCID 21923459, compound

Product 1

HCID 86594387HCID 86594387, compound

Conditions

Temperature
-78 °C

Procedure

LDA (2M in THF, 3.1 mL, 6.2 mmol) was added to a solution of 2,6-dimethylphenoxy propionate (1.10 g, 6.2 mmol) in anhydrous THF (12.4 mL) at −78° C., followed by stirring for 1 h at −78° C. The crude aldehyde 27 (4.1 mmol) from above dissolved in anhydrous THF (10 mL) was added slowly at −78° C. After 2 h at room temperature, the mixture was quenched with saturated aqueous NH4Cl (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic layer was dried over anhydrous MgSO4, evaporated and chromatographed (hexane/EtOAc 4:1) to yield 29 (1.67 g, 2.99 mmol) as a colorless oil: IR (CHCl3) 3120, 2857, 1744, 1514, 1216, 1099 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.26 (d, 2H, J=8.4 Hz), 6.87 (d, 2H, J=8.4 Hz), 4.62 (d, 1H, J=11.1 Hz), 4.40 (d, 1H, J=11.1 Hz), 4.06 (d, 1H, J=6.8 Hz), 3.79 (s, 3H), 3.66-3.61 (m, 3H), 2.89 (m, 1H), 2.19 (s, 6H), 1.86 (m, 2H), 1.55 (m, 3H), 1.27 (d, 3H, J=6.8 Hz), 1.01 (d, 3H, J=6.9 Hz), 0.93 (s, 9H), 0.07 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 173.5, 159.2, 148.0, 130.0, 129.9, 129.4, 128.4, 125.6, 113.8, 83.5, 70.7, 62.9, 55.1, 44.0, 35.6, 28.7, 26.6, 25.8, 18.2, 16.3, 14.2, 5.7, −5.3; HRMS (EI) calcd for C32H50O6Si 558.3377, found 558.3392.

Workup

  1. additionwas added slowly at −78° C
  2. waitAfter 2 h at room temperature
  3. customthe mixture was quenched with saturated aqueous NH4Cl (10 mL)
  4. extractionextracted with CH2Cl2 (3×10 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  6. customevaporated
  7. customchromatographed (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-604a9baaa96b46bc88dbac7fb3dedbcc
Source dataset
uspto-grants-2011_06
Patent number
US07968736B2

Reaction notes

Loading…