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

HRID 47999Notes

Reaction equation

HRID 47999 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.[Cl-].[NH4+]>ClCCl>[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 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of LiBH4 (0.78 g, 33 mmol) in dichloromethane (55 mL) was added methanol (1.04 g, 33 mmol) at rt. After the addition of 3-(3-{2-[3-(2-ethoxycarbonyl-2-methyl-propyl)-phenyl]-[1,3]dithian-2-yl }-phenyl)-2,2-dimethyl-propanoic acid ethyl ester (6.5 g, 12.2 mmol), the reaction mixture was heated to reflux for 6 h. After cooling to rt, saturated ammonium chloride solution (20 mL) and dichloromethane (15 mL) were added. The layers were separated and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford crude 3-(3-{2-[3-(3-hydroxy-2,2-dimethyl-propyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethyl-propan-1-ol (4.66g, 85%) as an oil. 1H NMR (300 MHz, CDCl3): δ (ppm): 7.6-6.8 (m, 8H), 3.63 (s, 4H), 3.16 (s, 4H), 2.95-2.60 (m, 4H), 2.0-1.8 (m, 2H), 1.61 (s, 2H), 0.75 (s, 12H). 13C NMR (75 MHz, CDCl3): δ (ppm): 142.4, 139.2, 131.7, 128.9, 128.1, 127.0, 71.1, 44.9, 43.7, 36.7, 29.6, 27.3, 24.2.

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 dichloromethane (2×10 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-059deea5e8784344942325a81e61d62f
Source dataset
uspto-grants-2004_03
Patent number
US06699910B2

Reaction notes

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