Triethylamine → Methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propyl ester

HRID 10671Notes

Reaction equation

HRID 10671 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][CH:8]([C:11]([CH3:19])([CH3:18])[O:12][SiH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:29](Cl)([CH3:32])(=[O:31])=[O:30]>ClCCl.O.C(OCC)(=O)C>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][CH:8]([C:11]([CH3:19])([CH3:18])[O:12][SiH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][O:10][S:29]([CH3:32])(=[O:31])=[O:30])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1317258993-(Tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propan-1-ol

Product 1

HCID 131725898Methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propyl esterYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Ex-50A: To a solution of 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propan-1-ol (25.0 g, 74.3 mmol) and triethylamine (22.6 g, 223 mmol) in dichloromethane (150 mL) at 0° C. was added mesyl chloride (12.8 g, 111 mmol) and the resulting slurry was stirred at 0° C. for 15 min and allowed to warm to rt. The solution was stirred for an additional 3 h at rt and diluted with water (130 mL) and ethyl acetate (350 mL). The layers were separated and the aqueous was extracted with ethyl acetate (1×150 mL). The combined organic extracts were washed with a saturated sodium bicarbonate (1×200 mL), a 50% sodium chloride solution (2×200 mL), dried over sodium sulfate and concentrated to afford 29.5 g (97%) of the expected methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propyl ester as a yellow oil, 97% yield. 1H-NMR (300 MHz, CDCl3) δ 4.29 (d, 2H, J=5.7 Hz), 3.61–3.68 (m, 4H), 2.99 (s, 3H), 2.04–2.11 (m, 1H), 0.88 (s, 18H), 0.049 (s, 12H). HRMS (ESI) Calcd. for C17H40O5SSi2: 413.2213. Found 413.2226.

Workup

  1. temperatureto warm to rt
  2. stirringThe solution was stirred for an additional 3 h at rt
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with ethyl acetate (1×150 mL)
  5. washThe combined organic extracts were washed with a saturated sodium bicarbonate (1×200 mL)
  6. dry with materiala 50% sodium chloride solution (2×200 mL), dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6ea7adcba54e488794a8fbab596dfcd5
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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