Imidazole → tert-Butyl-diphenyl-[5-(tetrahydro-pyran-2-yloxy)-pent-2-ynyloxy]-silane

HRID 1514334Notes

Reaction equation

HRID 1514334 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]#[C:11][CH2:12][OH:13].N1C=CN=C1.[CH3:19][C:20]([Si:23](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:22])[CH3:21]>C(Cl)Cl>[C:20]([Si:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[O:13][CH2:12][C:11]#[C:10][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)([CH3:22])([CH3:19])[CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 110414015-(Tetrahydro-pyran-2-yloxy)-pent-2-yn-1-ol

Product 1

HCID 57829244tert-Butyl-diphenyl-[5-(tetrahydro-pyran-2-yloxy)-pent-2-ynyloxy]-silaneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of compound 3 and imidazole in CH2Cl2 was treated with TBDPSCl dropwise at 0° C. for 2 h. The reaction mixture was diluted with CH2Cl2 (300 mL) and washed with water (200 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified with 10% EtOAc in hexanes by silica gel column chromatography to give 18.0 g of compound 4 (42.6 mmol, 96% yield): 1H NMR (CDCl3) δ 7.80˜7.64 (m, 4H), 7.49˜7.34 (m, 6H), 4.63 (t, J=3.6 Hz, 1H), 4.31 (t, J=1.9 Hz, 2H), 3.93˜3.83 (m, 1H), 3.77 (dt, J=9.7, 7.1 Hz, 1H), 3.55˜3.44 (m, 2H), 2.48 (tt, J=7.1, 2.1 Hz, 2H), 1.89˜1.46 (m, 6H), 1.06 (s, 9H).

Workup

  1. washwashed with water (200 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified with 10% EtOAc in hexanes by silica gel column chromatography

Sources & evidence

ORD record
ord-991ce6b886c3420ca32234bdb3b0b8f1
Source dataset
uspto-grants-2012_07
Patent number
US08222257B2

Reaction notes

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