Triethylamine → 2-(2-tert-Butyldimethylsilyloxyethoxy)-2-oxo-1,3,2-dioxaphospholane

HRID 21421Notes

Reaction equation

HRID 21421 reaction equation
Cl[P:2]1(=[O:7])[O:6][CH2:5][CH2:4][O:3]1.[Si:8]([O:15][CH2:16][CH2:17][OH:18])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].C(N(CC)CC)C>ClCCl>[Si:8]([O:15][CH2:16][CH2:17][O:18][P:2]1(=[O:7])[O:6][CH2:5][CH2:4][O:3]1)([C:11]([CH3:13])([CH3:14])[CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 810872-Chloro-1,3,2-dioxaphospholane 2-oxideHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol

Product 1

HCID 233614712-(2-tert-Butyldimethylsilyloxyethoxy)-2-oxo-1,3,2-dioxaphospholane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of freshly prepared 2-chloro-2-oxo-1,3,2-dioxaphospholane (14.2 g, 0.1M) in dry dichloromethane (30 ml) was added, drop-wise, to a stirred mixture of 2-(tert-butyldimethylsilyloxy)ethanol (17.6 g, 0.1M), triethylamine (18.1 ml, 0.13M) in dry dichloromethane (30 ml) at 0° C. under a nitrogen atmosphere. The mixture was allowed to warm to ambient temperature and was stirred for a further 2 hours. The mixture was filtered and the filtrand washed with n-hexane. The filtrate was evaporated in vacuo, diluted with n-hexane (30 ml) filtered and the filtrate evaporated in vacuo to give a brown oil.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrand washed with n-hexane
  3. customThe filtrate was evaporated in vacuo
  4. additiondiluted with n-hexane (30 ml)
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customto give a brown oil

Sources & evidence

ORD record
ord-b3a11a8e97104243b03dc83a0ee2e8cf
Source dataset
uspto-grants-1995_06
Patent number
US05422402

Reaction notes

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