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

HRID 239070Notes

Reaction equation

HRID 239070 reaction equation
[Li+].[BH4-].CO.C([O:7][C:8](=O)[C:9]([CH3:39])([CH3:38])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]([C:33](OCC)=[O:34])([CH3:32])[CH3:31])[CH:24]=3)[S:22][CH2:21][CH2:20][CH2:19][S:18]2)[CH:12]=1)C.[NH4+].[Cl-]>C(Cl)Cl>[OH:7][CH2:8][C:9]([CH3:39])([CH3:38])[CH2:10][C:11]1[CH:12]=[C:13]([C:17]2([C:23]3[CH:24]=[C:25]([CH2:29][C:30]([CH3:32])([CH3:31])[CH2:33][OH:34])[CH:26]=[CH:27][CH:28]=3)[S:18][CH2:19][CH2:20][CH2:21][S:22]2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 113185153-(3-{2-[3-(2-Ethoxycarbonyl-2-methyl-propyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethyl-propanoic acid ethyl ester

Product 1

HCID 114649623-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-olYield 85.2%

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., 2 H), 7.17 (m, 4 H), 6.97 (m, 2 H), 3.63 (s, 4 H), 3.16 (s, 4 H), 2.69 (m, 2 H), 2.47 (m, 4 H), 1.88 (m, 2 H), 0.75 (s, 12 H). 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-c09087bfb0c44c84a21ca33a8af7d762
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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