Methanol → 3-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol

HRID 873283Notes

Reaction equation

HRID 873283 reaction equation
[Li+].[BH4-].[CH3:3][OH:4].C(OC(=O)C(C)(C)C[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]([C:33](OCC)=[O:34])([CH3:32])[CH3:31])[CH:24]=2)[S:22][CH2:21][CH2:20][CH2:19][S:18]1)C.[NH4+].[Cl-]>C(Cl)Cl>[OH:34][CH2:33][C:30]([CH3:31])([CH3:32])[CH2:29][C:25]1[CH:24]=[C:23]([C:17]2([C:12]3[CH:11]=[C:16]([CH2:11][C:12]([CH3:17])([CH3:13])[CH2:3][OH:4])[CH:15]=[CH:14][CH:13]=3)[S:18][CH2:19][CH2:20][CH2:21][S:22]2)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 86729799HCID 86729799, compound

Product 1

HCID 114649623-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-olYield 170.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of LiBH4 (0.78 g, 35.8 mmol) in CH2Cl2 (55 mL) was added methanol (1.04 g, 32.5 mmol) at room temperature. After the addition of 229 (6.5 g, 12.3 mmol), the reaction mixture was heated to reflux for 6 h. After cooling to room temperature, saturated aqueous NH4Cl solution (20 mL) and CH2Cl2 (15 mL) were added and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to afford 230 (4.66 g, 85%) as an oil. 1H NMR (CDCl3): δ 7.42 (s br., 2H), 7.17 (m, 4H), 6.97 (m, 2H), 3.63 (s, 4H), 3.16 (s, 4H), 2.69 (m, 2H), 2.47 (m, 4H), 1.88 (m, 2H), 0.75 (s, 12H). 13C NMR (CDCl3): δ 142.39, 139.18, 131.69, 129.88, 128.05, 127.01, 71.12, 44.89, 43.74, 36.70, 29.63, 24.22.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8bcb63814f6f4a59abd05bb6cc810103
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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